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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-01-08 17:23:42 UTC

Update Date

2022-03-07 02:51:10 UTC

HMDB ID

HMDB0011511

Secondary Accession Numbers

HMDB11511

Metabolite Identification

Common Name

LysoPE(20:0/0:0)

Description

LysoPE(20:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

      
  Mrv1652303201821122D          

 35 34  0  0  1  0            999 V2000
   18.3996  -13.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7246  -13.9577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0495  -13.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0748  -13.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3745  -13.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1978  -14.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7497  -13.5680    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.3600  -12.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1395  -14.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4248  -13.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0999  -13.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7749  -13.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4501  -13.5680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3123  -14.7669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5150  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3726  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0871  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8015  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5159  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2303  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9448  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6591  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3735  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0879  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8024  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5168  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2313  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9456  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6600  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6600  -12.7203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34  5  1  0  0  0  0
 34 35  2  0  0  0  0
M  END

HMDB0011511
     RDKit          3D
LysoPE(20:0/0:0)
 86 85  0  0  0  0  0  0  0  0999 V2000
  -10.7613    3.9277    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6770    2.8418    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1326    2.8024   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0363    1.7473   -1.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5130    0.3932   -0.8461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4731   -0.6663   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3214   -0.6722   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3492    0.4301    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    0.7752   -1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8610   -0.3001   -1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -0.7911   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7969    0.2679   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161   -0.2986    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -0.8692    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -1.4352    2.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -2.5247    1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -3.1526    2.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444   -4.2409    1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -3.8080    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924   -2.8068    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -2.4667    2.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7239   -2.2229   -0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -1.2780    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8526   -1.8382    1.0297 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3940   -2.9308    0.3301 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9195   -0.7507    1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2749   -0.3846   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4465    0.8100   -0.0831 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1340    1.7870    1.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9756    0.1227    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5212    1.6899   -1.5177 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3490    2.7912   -1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4384    3.6018   -2.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250    4.0816   -3.0223 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8392    4.2998    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4223    4.7176   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6876    3.4340   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1666    1.9175    0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9024    3.0736    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6180    3.7856   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8935    2.6880   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6736    1.7076   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2047    2.1606   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3603    0.1452   -1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0421    0.3401    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1839   -0.8539   -2.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0453   -1.6431   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7413   -1.6398   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7292   -0.7711    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4792    0.0117    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    1.3300    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340    1.2074   -2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567    1.6272   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5415   -1.1655   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5052    0.0225   -2.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -1.5328   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -1.2817   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197    0.7328   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722    1.0907   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -1.0610   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    0.5219    0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -1.7724    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.1000    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8698   -1.9135    3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -0.6545    2.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482   -3.2836    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9963   -2.1224    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -2.3898    3.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -3.6891    3.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -4.7070    2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -4.9750    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2443   -3.4259   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -4.6837    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2317   -0.4139    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0990   -0.8300   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -2.1228    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556   -3.6862    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8077   -1.1668    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4846    0.1008    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0473   -0.1150    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9454    3.4156   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3627    2.4399   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1524    4.4287   -2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316    2.9272   -3.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6701    4.5545   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1864    4.6880   -3.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 17 69  1  0
 18 70  1  0
 18 71  1  0
 19 72  1  0
 19 73  1  0
 23 74  1  0
 23 75  1  0
 24 76  1  1
 25 77  1  0
 26 78  1  0
 26 79  1  0
 30 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 34 85  1  0
 34 86  1  0
M  END

      
  Mrv1652303201821122D          

 35 34  0  0  1  0            999 V2000
   18.3996  -13.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7246  -13.9577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0495  -13.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0748  -13.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3745  -13.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1978  -14.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7497  -13.5680    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.3600  -12.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1395  -14.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4248  -13.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0999  -13.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7749  -13.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4501  -13.5680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3123  -14.7669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5150  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3726  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0871  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8015  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5159  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2303  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9448  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6591  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3735  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0879  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8024  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5168  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2313  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9456  -13.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6600  -13.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6600  -12.7203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34  5  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011511

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCN

> <INCHI_IDENTIFIER>
InChI=1S/C25H52NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26/h24,27H,2-23,26H2,1H3,(H,29,30)/t24-/m1/s1

> <INCHI_KEY>
HEQMDGOBDIGJOC-XMMPIXPASA-N

> <FORMULA>
C25H52NO7P

> <MOLECULAR_WEIGHT>
509.6566

> <EXACT_MASS>
509.348139535

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.79075287729078

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-2-hydroxy-3-(icosanoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
5.308136086475666

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.655705215902849

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8690837557474262

> <JCHEM_PKA_STRONGEST_BASIC>
9.999833383834863

> <JCHEM_POLAR_SURFACE_AREA>
128.31

> <JCHEM_REFRACTIVITY>
135.81650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy((2R)-2-hydroxy-3-(icosanoyloxy)propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011511
     RDKit          3D
LysoPE(20:0/0:0)
 86 85  0  0  0  0  0  0  0  0999 V2000
  -10.7613    3.9277    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6770    2.8418    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1326    2.8024   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0363    1.7473   -1.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5130    0.3932   -0.8461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4731   -0.6663   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3214   -0.6722   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3492    0.4301    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    0.7752   -1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8610   -0.3001   -1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -0.7911   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7969    0.2679   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161   -0.2986    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -0.8692    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -1.4352    2.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -2.5247    1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -3.1526    2.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444   -4.2409    1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -3.8080    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924   -2.8068    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -2.4667    2.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7239   -2.2229   -0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -1.2780    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8526   -1.8382    1.0297 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3940   -2.9308    0.3301 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9195   -0.7507    1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2749   -0.3846   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4465    0.8100   -0.0831 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1340    1.7870    1.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9756    0.1227    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5212    1.6899   -1.5177 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3490    2.7912   -1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4384    3.6018   -2.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250    4.0816   -3.0223 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8392    4.2998    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4223    4.7176   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6876    3.4340   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1666    1.9175    0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9024    3.0736    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6180    3.7856   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8935    2.6880   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6736    1.7076   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2047    2.1606   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3603    0.1452   -1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0421    0.3401    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1839   -0.8539   -2.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0453   -1.6431   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7413   -1.6398   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7292   -0.7711    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4792    0.0117    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    1.3300    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340    1.2074   -2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567    1.6272   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5415   -1.1655   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5052    0.0225   -2.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -1.5328   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -1.2817   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197    0.7328   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722    1.0907   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -1.0610   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    0.5219    0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -1.7724    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.1000    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8698   -1.9135    3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -0.6545    2.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482   -3.2836    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9963   -2.1224    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -2.3898    3.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -3.6891    3.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -4.7070    2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -4.9750    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2443   -3.4259   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -4.6837    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2317   -0.4139    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0990   -0.8300   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -2.1228    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556   -3.6862    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8077   -1.1668    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4846    0.1008    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0473   -0.1150    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9454    3.4156   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3627    2.4399   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1524    4.4287   -2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316    2.9272   -3.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6701    4.5545   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1864    4.6880   -3.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 17 69  1  0
 18 70  1  0
 18 71  1  0
 19 72  1  0
 19 73  1  0
 23 74  1  0
 23 75  1  0
 24 76  1  1
 25 77  1  0
 26 78  1  0
 26 79  1  0
 30 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 34 85  1  0
 34 86  1  0
M  END

HEADER    PROTEIN                                 20-MAR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-18         0                                  
HETATM    1  C   UNK     0      34.346 -25.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.086 -26.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.826 -25.327   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      35.606 -26.054   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.566 -26.054   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      32.103 -27.510   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      36.866 -25.327   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      36.139 -24.067   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      37.594 -26.587   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      38.126 -24.599   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      39.386 -25.327   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.647 -24.599   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      41.907 -25.327   0.000  0.00  0.00           N+0
HETATM   14  H   UNK     0      34.183 -27.565   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       3.894 -26.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.228 -25.284   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.561 -26.054   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.895 -25.284   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.228 -26.054   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.562 -25.284   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.896 -26.054   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.229 -25.284   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.563 -26.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.896 -25.284   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.230 -26.054   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.564 -25.284   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.897 -26.054   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.231 -25.284   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.564 -26.054   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.898 -25.284   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.231 -26.054   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.565 -25.284   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.899 -26.054   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.232 -25.284   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      29.232 -23.745   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   14                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   34                                                       
CONECT    6    2                                                            
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    2                                                            
CONECT   15   16                                                            
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    5   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END

COMPND    HMDB0011511
HETATM    1  C1  UNL     1     -10.761   3.928   0.282  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.677   2.842   0.287  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.133   2.802  -1.112  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.036   1.747  -1.177  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.513   0.393  -0.846  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.473  -0.666  -0.926  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.321  -0.672  -0.029  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.349   0.430   0.017  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.658   0.775  -1.256  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.861  -0.300  -1.895  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.761  -0.791  -1.001  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.797   0.268  -0.603  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.716  -0.299   0.275  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.317  -0.869   1.517  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.270  -1.435   2.475  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.471  -2.525   1.775  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.530  -3.153   2.666  1.00  0.00           C  
HETATM   18  C18 UNL     1       2.244  -4.241   1.917  1.00  0.00           C  
HETATM   19  C19 UNL     1       2.938  -3.808   0.677  1.00  0.00           C  
HETATM   20  C20 UNL     1       3.992  -2.807   1.010  1.00  0.00           C  
HETATM   21  O1  UNL     1       4.248  -2.467   2.182  1.00  0.00           O  
HETATM   22  O2  UNL     1       4.724  -2.223  -0.007  1.00  0.00           O  
HETATM   23  C21 UNL     1       5.732  -1.278   0.220  1.00  0.00           C  
HETATM   24  C22 UNL     1       6.853  -1.838   1.030  1.00  0.00           C  
HETATM   25  O3  UNL     1       7.394  -2.931   0.330  1.00  0.00           O  
HETATM   26  C23 UNL     1       7.919  -0.751   1.143  1.00  0.00           C  
HETATM   27  O4  UNL     1       8.275  -0.385  -0.162  1.00  0.00           O  
HETATM   28  P1  UNL     1       9.447   0.810  -0.083  1.00  0.00           P  
HETATM   29  O5  UNL     1       9.134   1.787   1.033  1.00  0.00           O  
HETATM   30  O6  UNL     1      10.976   0.123   0.202  1.00  0.00           O  
HETATM   31  O7  UNL     1       9.521   1.690  -1.518  1.00  0.00           O  
HETATM   32  C24 UNL     1      10.349   2.791  -1.378  1.00  0.00           C  
HETATM   33  C25 UNL     1      10.438   3.602  -2.646  1.00  0.00           C  
HETATM   34  N1  UNL     1       9.125   4.082  -3.022  1.00  0.00           N  
HETATM   35  H1  UNL     1     -10.839   4.300   1.326  1.00  0.00           H  
HETATM   36  H2  UNL     1     -10.422   4.718  -0.415  1.00  0.00           H  
HETATM   37  H3  UNL     1     -11.688   3.434  -0.066  1.00  0.00           H  
HETATM   38  H4  UNL     1     -10.167   1.917   0.598  1.00  0.00           H  
HETATM   39  H5  UNL     1      -8.902   3.074   1.040  1.00  0.00           H  
HETATM   40  H6  UNL     1      -8.618   3.786  -1.281  1.00  0.00           H  
HETATM   41  H7  UNL     1      -9.894   2.688  -1.881  1.00  0.00           H  
HETATM   42  H8  UNL     1      -7.674   1.708  -2.255  1.00  0.00           H  
HETATM   43  H9  UNL     1      -7.205   2.161  -0.622  1.00  0.00           H  
HETATM   44  H10 UNL     1      -9.360   0.145  -1.571  1.00  0.00           H  
HETATM   45  H11 UNL     1      -9.042   0.340   0.147  1.00  0.00           H  
HETATM   46  H12 UNL     1      -7.184  -0.854  -2.012  1.00  0.00           H  
HETATM   47  H13 UNL     1      -8.045  -1.643  -0.704  1.00  0.00           H  
HETATM   48  H14 UNL     1      -5.741  -1.640  -0.138  1.00  0.00           H  
HETATM   49  H15 UNL     1      -6.729  -0.771   1.038  1.00  0.00           H  
HETATM   50  H16 UNL     1      -4.479   0.012   0.681  1.00  0.00           H  
HETATM   51  H17 UNL     1      -5.607   1.330   0.589  1.00  0.00           H  
HETATM   52  H18 UNL     1      -5.334   1.207  -2.025  1.00  0.00           H  
HETATM   53  H19 UNL     1      -3.957   1.627  -1.008  1.00  0.00           H  
HETATM   54  H20 UNL     1      -4.542  -1.166  -2.075  1.00  0.00           H  
HETATM   55  H21 UNL     1      -3.505   0.023  -2.887  1.00  0.00           H  
HETATM   56  H22 UNL     1      -2.179  -1.533  -1.620  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.227  -1.282  -0.144  1.00  0.00           H  
HETATM   58  H24 UNL     1      -1.320   0.733  -1.505  1.00  0.00           H  
HETATM   59  H25 UNL     1      -2.272   1.091  -0.006  1.00  0.00           H  
HETATM   60  H26 UNL     1      -0.188  -1.061  -0.352  1.00  0.00           H  
HETATM   61  H27 UNL     1      -0.021   0.522   0.554  1.00  0.00           H  
HETATM   62  H28 UNL     1      -1.950  -1.772   1.266  1.00  0.00           H  
HETATM   63  H29 UNL     1      -1.933  -0.100   1.994  1.00  0.00           H  
HETATM   64  H30 UNL     1      -0.870  -1.914   3.301  1.00  0.00           H  
HETATM   65  H31 UNL     1       0.363  -0.654   2.898  1.00  0.00           H  
HETATM   66  H32 UNL     1      -0.248  -3.284   1.419  1.00  0.00           H  
HETATM   67  H33 UNL     1       0.996  -2.122   0.873  1.00  0.00           H  
HETATM   68  H34 UNL     1       2.175  -2.390   3.101  1.00  0.00           H  
HETATM   69  H35 UNL     1       0.945  -3.689   3.475  1.00  0.00           H  
HETATM   70  H36 UNL     1       2.980  -4.707   2.609  1.00  0.00           H  
HETATM   71  H37 UNL     1       1.456  -4.975   1.614  1.00  0.00           H  
HETATM   72  H38 UNL     1       2.244  -3.426  -0.100  1.00  0.00           H  
HETATM   73  H39 UNL     1       3.444  -4.684   0.224  1.00  0.00           H  
HETATM   74  H40 UNL     1       5.232  -0.414   0.745  1.00  0.00           H  
HETATM   75  H41 UNL     1       6.099  -0.830  -0.739  1.00  0.00           H  
HETATM   76  H42 UNL     1       6.498  -2.123   2.022  1.00  0.00           H  
HETATM   77  H43 UNL     1       7.556  -3.686   0.961  1.00  0.00           H  
HETATM   78  H44 UNL     1       8.808  -1.167   1.626  1.00  0.00           H  
HETATM   79  H45 UNL     1       7.485   0.101   1.694  1.00  0.00           H  
HETATM   80  H46 UNL     1      11.047  -0.115   1.158  1.00  0.00           H  
HETATM   81  H47 UNL     1       9.945   3.416  -0.543  1.00  0.00           H  
HETATM   82  H48 UNL     1      11.363   2.440  -1.092  1.00  0.00           H  
HETATM   83  H49 UNL     1      11.152   4.429  -2.555  1.00  0.00           H  
HETATM   84  H50 UNL     1      10.832   2.927  -3.442  1.00  0.00           H  
HETATM   85  H51 UNL     1       8.670   4.555  -2.213  1.00  0.00           H  
HETATM   86  H52 UNL     1       9.186   4.688  -3.866  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   48   49
CONECT    8    9   50   51
CONECT    9   10   52   53
CONECT   10   11   54   55
CONECT   11   12   56   57
CONECT   12   13   58   59
CONECT   13   14   60   61
CONECT   14   15   62   63
CONECT   15   16   64   65
CONECT   16   17   66   67
CONECT   17   18   68   69
CONECT   18   19   70   71
CONECT   19   20   72   73
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   74   75
CONECT   24   25   26   76
CONECT   25   77
CONECT   26   27   78   79
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   80
CONECT   31   32
CONECT   32   33   81   82
CONECT   33   34   83   84
CONECT   34   85   86
END

HMDB0011511
     RDKit          3D
LysoPE(20:0/0:0)
 86 85  0  0  0  0  0  0  0  0999 V2000
  -10.7613    3.9277    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6770    2.8418    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1326    2.8024   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0363    1.7473   -1.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5130    0.3932   -0.8461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4731   -0.6663   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3214   -0.6722   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3492    0.4301    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581    0.7752   -1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8610   -0.3001   -1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -0.7911   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7969    0.2679   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161   -0.2986    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -0.8692    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -1.4352    2.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -2.5247    1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -3.1526    2.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444   -4.2409    1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -3.8080    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924   -2.8068    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -2.4667    2.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7239   -2.2229   -0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -1.2780    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8526   -1.8382    1.0297 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3940   -2.9308    0.3301 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9195   -0.7507    1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2749   -0.3846   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4465    0.8100   -0.0831 P   0  0  0  0  0  5  0  0  0  0  0  0
    9.1340    1.7870    1.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9756    0.1227    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5212    1.6899   -1.5177 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3490    2.7912   -1.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4384    3.6018   -2.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250    4.0816   -3.0223 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8392    4.2998    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4223    4.7176   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6876    3.4340   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1666    1.9175    0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9024    3.0736    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6180    3.7856   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8935    2.6880   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6736    1.7076   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2047    2.1606   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3603    0.1452   -1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0421    0.3401    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1839   -0.8539   -2.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0453   -1.6431   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7413   -1.6398   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7292   -0.7711    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4792    0.0117    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070    1.3300    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340    1.2074   -2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567    1.6272   -1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5415   -1.1655   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5052    0.0225   -2.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -1.5328   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -1.2817   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197    0.7328   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722    1.0907   -0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -1.0610   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    0.5219    0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -1.7724    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.1000    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8698   -1.9135    3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -0.6545    2.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482   -3.2836    1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9963   -2.1224    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -2.3898    3.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -3.6891    3.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -4.7070    2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -4.9750    1.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2443   -3.4259   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -4.6837    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2317   -0.4139    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0990   -0.8300   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -2.1228    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5556   -3.6862    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8077   -1.1668    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4846    0.1008    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0473   -0.1150    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9454    3.4156   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3627    2.4399   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1524    4.4287   -2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316    2.9272   -3.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6701    4.5545   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1864    4.6880   -3.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  8 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 12 59  1  0
 13 60  1  0
 13 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 16 66  1  0
 16 67  1  0
 17 68  1  0
 17 69  1  0
 18 70  1  0
 18 71  1  0
 19 72  1  0
 19 73  1  0
 23 74  1  0
 23 75  1  0
 24 76  1  1
 25 77  1  0
 26 78  1  0
 26 79  1  0
 30 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  0
 33 84  1  0
 34 85  1  0
 34 86  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Arachidonyl-2-hydroxy-sn-glycero-3-phosphoethanolamine	ChEBI
1-Arachidoyl-sn-glycero-3-phosphoethanolamine	ChEBI
1-Eicosanoyl-glycero-3-phosphoethanolamine	ChEBI
1-Eicosanoyl-sn-glycero-3-phosphoethanolamine	ChEBI
Eicosanoyl-lysophosphatidylethanolamine	ChEBI
LPE(20:0)	ChEBI
LPE(20:0/0:0)	ChEBI
Lyso-pe(20:0)	ChEBI
Lyso-pe(20:0/0:0)	ChEBI
LysoPE(20:0)	ChEBI
Lysophosphatidylethanolamine(20:0)	ChEBI
Lysophosphatidylethanolamine(20:0/0:0)	ChEBI
PE(20:0/0:0)	ChEBI
1-Eicosanoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine	HMDB
LysoPE(20:0/0:0)	Lipid Annotator
1-Arachidoylglycerophosphoethanolamine	HMDB
1-Eicosanoylglycerophosphoethanolamine	HMDB

Chemical Formula

C₂₅H₅₂NO₇P

Average Molecular Weight

509.6566

Monoisotopic Molecular Weight

509.348139535

IUPAC Name

(2-aminoethoxy)[(2R)-2-hydroxy-3-(icosanoyloxy)propoxy]phosphinic acid

Traditional Name

2-aminoethoxy((2R)-2-hydroxy-3-(icosanoyloxy)propoxy)phosphinic acid

CAS Registry Number

899445-69-3

SMILES

[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCN

InChI Identifier

InChI=1S/C25H52NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26/h24,27H,2-23,26H2,1H3,(H,29,30)/t24-/m1/s1

InChI Key

HEQMDGOBDIGJOC-XMMPIXPASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphoethanolamines. These are glycerophoethanolamines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphoethanolamine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

1-acyl-sn-glycero-3-phosphoethanolamines

Alternative Parents

Substituents

1-monoacyl-sn-glycero-3-phosphoethanolamine
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Monoacylglycerophosphoethanolamines (LMGP02050012 )

Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0011511)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22882828)

Cellular substructure

Membrane (HMDB: HMDB0011511)
Extracellular (HMDB: HMDB0011511)
Cell membrane (HMDB: HMDB0011511)
Intracellular membrane (HMDB: HMDB0011511)

Tissue

All Tissues (HMDB: HMDB0011511)
All Tissues (HMDB: HMDB0011511)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0011511)

Source

Endogenous

Endogenous (HMDB: HMDB0011511)

Animal

Animal (HMDB: HMDB0011511)

Exogenous

Food

Food (HMDB: HMDB0011511)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0011511)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0011511)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0011511)

Lipid metabolism pathway (HMDB: HMDB0011511)

Cellular process

Cell signaling (HMDB: HMDB0011511)

Biochemical process

Lipid transport (HMDB: HMDB0011511)

Role

Biological role

Energy source (HMDB: HMDB0011511)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0011511)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0011511)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00097 g/L	ALOGPS
logP	5.47	ALOGPS
logP	5.31	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.31 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	135.82 m³·mol⁻¹	ChemAxon
Polarizability	60.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	229.773	31661259
DarkChem	[M-H]-	227.403	31661259
DeepCCS	[M+H]+	203.168	30932474
DeepCCS	[M-H]-	200.81	30932474
DeepCCS	[M-2H]-	234.16	30932474
DeepCCS	[M+Na]+	209.383	30932474
AllCCS	[M+H]+	233.2	32859911
AllCCS	[M+H-H2O]+	231.8	32859911
AllCCS	[M+NH4]+	234.5	32859911
AllCCS	[M+Na]+	234.8	32859911
AllCCS	[M-H]-	225.5	32859911
AllCCS	[M+Na-2H]-	228.7	32859911
AllCCS	[M+HCOO]-	232.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.18 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6639 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	83.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2723.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	184.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	230.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	581.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	732.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	718.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	659.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1504.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	642.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1433.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	609.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	291.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	113.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	71.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LysoPE(20:0/0:0)	[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCN	3654.2	Standard polar	33892256
LysoPE(20:0/0:0)	[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCN	3455.7	Standard non polar	33892256
LysoPE(20:0/0:0)	[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCN	3820.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LysoPE(20:0/0:0),1TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)O[Si](C)(C)C	3743.3	Semi standard non polar	33892256
LysoPE(20:0/0:0),1TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN)O[Si](C)(C)C	3758.3	Semi standard non polar	33892256
LysoPE(20:0/0:0),1TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN[Si](C)(C)C	3826.9	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C	3749.2	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C	3523.4	Standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)O[Si](C)(C)C	5222.1	Standard polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)O[Si](C)(C)C	3822.1	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)O[Si](C)(C)C	3680.8	Standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)O[Si](C)(C)C	5091.5	Standard polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C	3810.4	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C	3711.2	Standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C	4493.2	Standard polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #4	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	4033.7	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #4	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	3727.3	Standard non polar	33892256
LysoPE(20:0/0:0),2TMS,isomer #4	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C	5107.8	Standard polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3805.6	Semi standard non polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3678.1	Standard non polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	4202.5	Standard polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	4054.3	Semi standard non polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3717.9	Standard non polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	4759.0	Standard polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	4054.3	Semi standard non polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3741.0	Standard non polar	33892256
LysoPE(20:0/0:0),3TMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	4295.2	Standard polar	33892256
LysoPE(20:0/0:0),4TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	4073.6	Semi standard non polar	33892256
LysoPE(20:0/0:0),4TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3717.0	Standard non polar	33892256
LysoPE(20:0/0:0),4TMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	4045.8	Standard polar	33892256
LysoPE(20:0/0:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)O[Si](C)(C)C(C)(C)C	4022.9	Semi standard non polar	33892256
LysoPE(20:0/0:0),1TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C	3998.0	Semi standard non polar	33892256
LysoPE(20:0/0:0),1TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C	4089.0	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4245.9	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3752.3	Standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	5116.3	Standard polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4320.5	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3917.5	Standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4977.8	Standard polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4311.0	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3935.9	Standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4539.4	Standard polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #4	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4521.9	Semi standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #4	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3939.9	Standard non polar	33892256
LysoPE(20:0/0:0),2TBDMS,isomer #4	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	5008.5	Standard polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4541.4	Semi standard non polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4018.5	Standard non polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #1	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4334.6	Standard polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4790.6	Semi standard non polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4060.9	Standard non polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #2	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4692.1	Standard polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4764.6	Semi standard non polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4062.0	Standard non polar	33892256
LysoPE(20:0/0:0),3TBDMS,isomer #3	CCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4396.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPE(20:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbc-3920200000-0efc847bf5001cdfad4b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - LysoPE(20:0/0:0) GC-MS (1 TMS) - 70eV, Positive	splash10-0329-4190200000-89f10b5cb2675325d2ae	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 10V, Positive-QTOF	splash10-0006-9111010000-069aa0725da01d787102	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 20V, Positive-QTOF	splash10-0006-9121000000-cd2b0817372d87a2355e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 40V, Positive-QTOF	splash10-0006-9130000000-666de551a7fd28da0703	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 10V, Negative-QTOF	splash10-06r6-2489550000-be9fc03087bf42ca1d35	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 20V, Negative-QTOF	splash10-01r6-9657100000-e61378182869ee0ed889	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 40V, Negative-QTOF	splash10-01t9-9100000000-eb380163bfa7f2f0ba11	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 10V, Positive-QTOF	splash10-03di-3003090000-c13188261dabdfec0410	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 20V, Positive-QTOF	splash10-00kf-9104200000-5d1a70f68aa386e775ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 40V, Positive-QTOF	splash10-0006-9300000000-92a9f11483cee2b5cd75	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 10V, Negative-QTOF	splash10-0a4i-0000490000-f1ea2cdea550e326a305	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 20V, Negative-QTOF	splash10-03di-2539240000-133a041f021264a70bb2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - LysoPE(20:0/0:0) 40V, Negative-QTOF	splash10-03di-1309000000-9cb5913bfb8193d93150	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hepatocellular carcinoma	22882828	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Liver Cirrhosis	22882828	details

Associated Disorders and Diseases

Disease References

Hepatocellular carcinoma
Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]
Cirrhosis
Ressom HW, Xiao JF, Tuli L, Varghese RS, Zhou B, Tsai TH, Ranjbar MR, Zhao Y, Wang J, Di Poto C, Cheema AK, Tadesse MG, Goldman R, Shetty K: Utilization of metabolomics to identify serum biomarkers for hepatocellular carcinoma in patients with liver cirrhosis. Anal Chim Acta. 2012 Sep 19;743:90-100. doi: 10.1016/j.aca.2012.07.013. Epub 2012 Jul 20. [PubMed:22882828 ]

Associated OMIM IDs

114550 (Hepatocellular carcinoma)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028227

KNApSAcK ID

Not Available

Chemspider ID

24769389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52925131

PDB ID

Not Available

ChEBI ID

131690

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:: ENPP2
Uniprot ID:: Q13822
Molecular weight:: 98992.78

Showing metabocard for LysoPE(20:0/0:0) (HMDB0011511)

MOL for HMDB0011511 (LysoPE(20:0/0:0))

3D MOL for HMDB0011511 (LysoPE(20:0/0:0))

3D SDF for HMDB0011511 (LysoPE(20:0/0:0))

3D-SDF for HMDB0011511 (LysoPE(20:0/0:0))

PDB for HMDB0011511 (LysoPE(20:0/0:0))

3D PDB for HMDB0011511 (LysoPE(20:0/0:0))

SMILES for HMDB0011511 (LysoPE(20:0/0:0))

INCHI for HMDB0011511 (LysoPE(20:0/0:0))

Structure for HMDB0011511 (LysoPE(20:0/0:0))

3D Structure for HMDB0011511 (LysoPE(20:0/0:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes