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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 13:51:42 UTC

Update Date

2020-02-26 21:38:58 UTC

HMDB ID

HMDB0013631

Secondary Accession Numbers

HMDB13631

Metabolite Identification

Common Name

Oleoyl glycine

Description

N-oleoyl glycine is an acylglycine with oleoic acid (C18:1(9Z))moiety attached to glycine molecule. It is reported to be preferentially produced by human glycine N-acyltransferase-like 2 (hGLYATL2), a member of a gene family of 4 putative glycine conjugating enzymes, synthesizes various N-acyl glycines. Recombinantly expressed hGLYATL2 efficiently conjugated oleoyl-CoA, arachidonoyl-CoA, and other medium- and long-chain acyl-CoAs to glycine. The enzyme was specific for glycine as an acceptor molecule.

Structure

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

HMDB0013631
     RDKit          3D
Oleoyl glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
    7.9786    2.5739    1.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2064    1.7012    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8597    1.3778   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9761    0.5016   -1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6263    0.1920   -1.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7243   -0.5438   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -0.7843   -1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.5351   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.7803    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.3827    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -0.6710   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820   -1.5018    0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -1.7837   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4197   -2.5904    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9069   -1.8932    1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345   -0.5764    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7259   -0.7087    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2919    0.6257    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7270    1.6295    0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4234    0.7897   -0.4286 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9710    2.0874   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1308    2.0004   -1.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4981    0.8721   -1.9911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8663    3.0922   -2.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5304    2.1717    2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9092    2.5917    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2711    3.6077    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8895    2.1717   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7014    0.7444    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    0.8370    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3871    2.3358   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5673    0.9976   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -0.4296   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767   -0.5016   -2.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247    1.0990   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    0.0772   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879   -1.4850   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -1.4474   -2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175    0.1385   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -1.9216   -1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -2.4513   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.5313    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178    0.1935    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.3287   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -1.1121   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463   -0.9660    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797   -2.4575    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8005   -0.8800   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255   -2.4271   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -2.8308    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -3.5751    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -2.5201    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -1.7390    2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059   -0.0370    2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7887    0.1020    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990   -1.1769   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4593   -1.3832    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8560   -0.0451   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3417    2.4846    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2106    2.8217   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5695    3.5226   -1.4103 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  2  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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 24 61  1  0
M  END


  Mrv1652303102016522D          

 24 23  0  0  0  0            999 V2000
    6.6517   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3662  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0807   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7951  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5096   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2241  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9386   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6531  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3675   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0820   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7965  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5109   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2255  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9399   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6544  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3689   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0834  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -8.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -10.0186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2268   -9.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9412  -10.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6557   -9.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9413  -10.8435    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  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  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
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013631

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-

> <INCHI_KEY>
HPFXACZRFJDURI-KTKRTIGZSA-N

> <FORMULA>
C20H37NO3

> <MOLECULAR_WEIGHT>
339.5127

> <EXACT_MASS>
339.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.702558917864096

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(9Z)-octadec-9-enamido]acetic acid

> <ALOGPS_LOGP>
6.68

> <JCHEM_LOGP>
5.678515211333333

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.018755584127888

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046618031811936

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6781963756507396

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
100.20569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-oleoyl glycine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013631
     RDKit          3D
Oleoyl glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
    7.9786    2.5739    1.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2064    1.7012    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8597    1.3778   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9761    0.5016   -1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6263    0.1920   -1.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7243   -0.5438   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -0.7843   -1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.5351   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.7803    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.3827    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -0.6710   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820   -1.5018    0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -1.7837   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4197   -2.5904    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9069   -1.8932    1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345   -0.5764    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7259   -0.7087    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2919    0.6257    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7270    1.6295    0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4234    0.7897   -0.4286 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9710    2.0874   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1308    2.0004   -1.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4981    0.8721   -1.9911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8663    3.0922   -2.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5304    2.1717    2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9092    2.5917    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2711    3.6077    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8895    2.1717   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7014    0.7444    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    0.8370    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3871    2.3358   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5673    0.9976   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -0.4296   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767   -0.5016   -2.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247    1.0990   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    0.0772   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879   -1.4850   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -1.4474   -2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175    0.1385   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -1.9216   -1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -2.4513   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.5313    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178    0.1935    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.3287   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -1.1121   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463   -0.9660    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797   -2.4575    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8005   -0.8800   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255   -2.4271   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -2.8308    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -3.5751    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -2.5201    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -1.7390    2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059   -0.0370    2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7887    0.1020    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990   -1.1769   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4593   -1.3832    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8560   -0.0451   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3417    2.4846    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2106    2.8217   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5695    3.5226   -1.4103 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  2  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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 24 61  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      12.417 -17.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.750 -18.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.084 -17.931   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.418 -18.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.751 -17.931   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.085 -18.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.419 -17.931   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.752 -18.701   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.086 -17.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.420 -17.931   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.753 -18.701   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.087 -17.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.421 -18.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.754 -17.931   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.088 -18.701   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.422 -17.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.756 -18.701   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.089 -17.931   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      35.089 -16.391   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      36.423 -18.701   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      37.757 -17.931   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.090 -18.701   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      40.424 -17.931   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      39.090 -20.241   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0013631
HETATM    1  C1  UNL     1       7.979   2.574   1.626  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.206   1.701   0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.860   1.378  -0.178  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.976   0.502  -1.409  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.626   0.192  -1.980  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.724  -0.544  -0.997  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.421  -0.784  -1.703  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.480  -1.535  -0.766  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.211  -0.780   0.440  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.022  -0.383   0.800  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.172  -0.671  -0.004  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.182  -1.502   0.802  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.402  -1.784  -0.050  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.420  -2.590   0.679  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.907  -1.893   1.916  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.534  -0.576   1.597  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.726  -0.709   0.677  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.292   0.626   0.409  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.727   1.629   0.959  1.00  0.00           O  
HETATM   20  N1  UNL     1      -7.423   0.790  -0.429  1.00  0.00           N  
HETATM   21  C19 UNL     1      -7.971   2.087  -0.687  1.00  0.00           C  
HETATM   22  C20 UNL     1      -9.131   2.000  -1.577  1.00  0.00           C  
HETATM   23  O2  UNL     1      -9.498   0.872  -1.991  1.00  0.00           O  
HETATM   24  O3  UNL     1      -9.866   3.092  -2.002  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.530   2.172   2.520  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.909   2.592   1.935  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.271   3.608   1.416  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.889   2.172  -0.323  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.701   0.744   0.715  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.280   0.837   0.600  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.387   2.336  -0.475  1.00  0.00           H  
HETATM   32  H8  UNL     1       7.567   0.998  -2.190  1.00  0.00           H  
HETATM   33  H9  UNL     1       7.488  -0.430  -1.125  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.777  -0.502  -2.838  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.125   1.099  -2.322  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.527   0.077  -0.103  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.188  -1.485  -0.643  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.538  -1.447  -2.594  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.918   0.138  -2.011  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.654  -1.922  -1.347  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.108  -2.451  -0.469  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.070  -0.531   1.103  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.918   0.193   1.747  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.698   0.329  -0.148  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.044  -1.112  -0.974  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.446  -0.966   1.743  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.680  -2.458   1.031  1.00  0.00           H  
HETATM   48  H24 UNL     1      -2.800  -0.880  -0.530  1.00  0.00           H  
HETATM   49  H25 UNL     1      -2.025  -2.427  -0.900  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.254  -2.831   0.004  1.00  0.00           H  
HETATM   51  H27 UNL     1      -2.958  -3.575   0.968  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.667  -2.520   2.440  1.00  0.00           H  
HETATM   53  H29 UNL     1      -3.097  -1.739   2.642  1.00  0.00           H  
HETATM   54  H30 UNL     1      -4.806  -0.037   2.530  1.00  0.00           H  
HETATM   55  H31 UNL     1      -3.789   0.102   1.092  1.00  0.00           H  
HETATM   56  H32 UNL     1      -5.399  -1.177  -0.283  1.00  0.00           H  
HETATM   57  H33 UNL     1      -6.459  -1.383   1.164  1.00  0.00           H  
HETATM   58  H34 UNL     1      -7.856  -0.045  -0.857  1.00  0.00           H  
HETATM   59  H35 UNL     1      -8.342   2.485   0.296  1.00  0.00           H  
HETATM   60  H36 UNL     1      -7.211   2.822  -1.023  1.00  0.00           H  
HETATM   61  H37 UNL     1     -10.570   3.523  -1.410  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   56   57
CONECT   18   19   19   20
CONECT   20   21   58
CONECT   21   22   59   60
CONECT   22   23   23   24
CONECT   24   61
END

HMDB0013631
     RDKit          3D
Oleoyl glycine
 61 60  0  0  0  0  0  0  0  0999 V2000
    7.9786    2.5739    1.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2064    1.7012    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8597    1.3778   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9761    0.5016   -1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6263    0.1920   -1.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7243   -0.5438   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -0.7843   -1.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.5351   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.7803    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.3827    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718   -0.6710   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820   -1.5018    0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016   -1.7837   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4197   -2.5904    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9069   -1.8932    1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345   -0.5764    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7259   -0.7087    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2919    0.6257    0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7270    1.6295    0.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4234    0.7897   -0.4286 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9710    2.0874   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1308    2.0004   -1.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4981    0.8721   -1.9911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8663    3.0922   -2.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5304    2.1717    2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9092    2.5917    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2711    3.6077    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8895    2.1717   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7014    0.7444    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    0.8370    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3871    2.3358   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5673    0.9976   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -0.4296   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767   -0.5016   -2.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247    1.0990   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    0.0772   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879   -1.4850   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376   -1.4474   -2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175    0.1385   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -1.9216   -1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -2.4513   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.5313    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178    0.1935    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.3287   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -1.1121   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463   -0.9660    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797   -2.4575    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8005   -0.8800   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255   -2.4271   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -2.8308    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -3.5751    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -2.5201    2.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -1.7390    2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059   -0.0370    2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7887    0.1020    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990   -1.1769   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4593   -1.3832    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8560   -0.0451   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3417    2.4846    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2106    2.8217   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5695    3.5226   -1.4103 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  2  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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 24 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Elmiric acid	ChEBI
EMA-1	ChEBI
N-(9Z-Octadecenoyl)-glycine	ChEBI
Elmirate	Generator
(Z)-N-(1-oxo-9-Octadecenyl)glycine	HMDB
Acylglycine 18:1(9Z)	HMDB
NO-Gly	HMDB
N-Oleoylglycine	MeSH

Chemical Formula

C₂₀H₃₇NO₃

Average Molecular Weight

339.5127

Monoisotopic Molecular Weight

339.277344055

IUPAC Name

2-[(9Z)-octadec-9-enamido]acetic acid

Traditional Name

N-oleoyl glycine

CAS Registry Number

2601-90-3

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-

InChI Key

HPFXACZRFJDURI-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:73723 )
fatty amide (CHEBI:73723 )
fatty acid derivative (CHEBI:73723 )
N-acyl amines (LMFA08020082 )

Ontology

Not Available

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	0.00025 g/L	ALOGPS
logP	6.68	ALOGPS
logP	5.68	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	100.21 m³·mol⁻¹	ChemAxon
Polarizability	42.7 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]+	190.707	31661259
DarkChem	[M-H]-	189.308	31661259
DeepCCS	[M+H]+	191.981	30932474
DeepCCS	[M-H]-	189.431	30932474
DeepCCS	[M-2H]-	222.641	30932474
DeepCCS	[M+Na]+	199.27	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	190.0	32859911
AllCCS	[M+NH4]+	195.0	32859911
AllCCS	[M+Na]+	195.7	32859911
AllCCS	[M-H]-	190.0	32859911
AllCCS	[M+Na-2H]-	191.8	32859911
AllCCS	[M+HCOO]-	193.9	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.	10.05 minutes	32390414
Predicted by Siyang on May 30, 2022	22.0879 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.67 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3134.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	489.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	233.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	259.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	628.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	953.6 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	780.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	140.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2077.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	654.7 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	1877.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	718.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	520.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	461.6 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleoyl glycine	CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O	3608.8	Standard polar	33892256
Oleoyl glycine	CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O	2496.6	Standard non polar	33892256
Oleoyl glycine	CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O	2730.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oleoyl glycine,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C	2787.4	Semi standard non polar	33892256
Oleoyl glycine,1TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C	2809.6	Semi standard non polar	33892256
Oleoyl glycine,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2763.7	Semi standard non polar	33892256
Oleoyl glycine,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2771.8	Standard non polar	33892256
Oleoyl glycine,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2823.7	Standard polar	33892256
Oleoyl glycine,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	3023.5	Semi standard non polar	33892256
Oleoyl glycine,1TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3038.5	Semi standard non polar	33892256
Oleoyl glycine,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3241.3	Semi standard non polar	33892256
Oleoyl glycine,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3099.9	Standard non polar	33892256
Oleoyl glycine,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3009.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oleoyl glycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fxx-9880000000-5ae1ba2d79b16bf75157	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleoyl glycine GC-MS (1 TMS) - 70eV, Positive	splash10-010u-9552000000-71bc6c116dd87ceeca79	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleoyl glycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleoyl glycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Oleoyl glycine 10V, Positive-QTOF	splash10-0006-6079000000-9aca349fae181649423d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Positive-QTOF	splash10-056r-9140000000-e6d406dd27867e8a8098	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Positive-QTOF	splash10-056r-9410000000-c014f50241b7c1cab5f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 10V, Negative-QTOF	splash10-000i-0019000000-c91936bf7faa6f7e252f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Negative-QTOF	splash10-0079-7279000000-a948d894dd4aeb45947a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Negative-QTOF	splash10-05fu-9010000000-70aba59d12b1777e20b6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 10V, Negative-QTOF	splash10-000i-1009000000-30c3a690fbd89dd9372b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Negative-QTOF	splash10-00di-9002000000-7b142c09660037254c26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Negative-QTOF	splash10-00di-9000000000-25e5315d765107a9843a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 10V, Positive-QTOF	splash10-002f-6019000000-83a9c5534ab2a3cdd674	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Positive-QTOF	splash10-004i-9121000000-3bd27eb556983ed36c17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Positive-QTOF	splash10-0a6u-9100000000-e5ee0f1c1ddd84c6fe41	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	21 +/- 23 uM	Adult (>18 years old)	Both	Normal	21359215	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029608

KNApSAcK ID

Not Available

Chemspider ID

4941514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436908

PDB ID

Not Available

ChEBI ID

73723

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

Not Available

Showing metabocard for Oleoyl glycine (HMDB0013631)

MOL for HMDB0013631 (Oleoyl glycine)

3D MOL for HMDB0013631 (Oleoyl glycine)

3D SDF for HMDB0013631 (Oleoyl glycine)

3D-SDF for HMDB0013631 (Oleoyl glycine)

PDB for HMDB0013631 (Oleoyl glycine)

3D PDB for HMDB0013631 (Oleoyl glycine)

SMILES for HMDB0013631 (Oleoyl glycine)

INCHI for HMDB0013631 (Oleoyl glycine)

Structure for HMDB0013631 (Oleoyl glycine)

3D Structure for HMDB0013631 (Oleoyl glycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra