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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-03-31 19:58:49 UTC

Update Date

2022-10-24 19:45:31 UTC

HMDB ID

HMDB0241869

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine

Description

3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine is an acylcarnitine. More specifically, it is an 3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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


  Mrv1652303312121582D          

 29 28  0  0  0  0            999 V2000
    0.3316    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.1914    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    2.2539    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4586    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
M  CHG  2   3  -1  26   1
M  END

HMDB0241869
     RDKit          3D
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine
 60 59  0  0  0  0  0  0  0  0999 V2000
    6.0619   -1.5283    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653   -0.6502    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6065    0.2340    2.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2885    0.1255   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887    0.9639   -0.7179 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8723    1.7691   -2.0779 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.5425    3.2399   -1.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332    1.2084   -3.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5486    1.6436   -2.2087 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -1.6120    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -2.4080   -0.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.9447    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271   -1.1637   -0.9935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187   -0.0973    0.9928 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.5155    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311   -0.4492    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026    0.3141   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814    1.5652   -0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -0.3047   -0.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571    0.4609   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0600    0.1897   -2.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825   -1.2423   -3.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3975   -1.8163   -3.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -1.9930   -3.5474 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.2453    0.0659   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622    0.2199    0.6716 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.6565    1.4301    1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -0.8929    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6811    0.2570    1.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6787   -1.0127    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6940   -1.7212    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6662   -2.4382    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061    0.5490    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220    1.1883    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274   -0.3317    2.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482    0.7720    0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6628   -0.5772   -1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    1.1228   -4.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9319    2.0468   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -2.2710    1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608   -1.9205   -1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983    0.0976    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    1.1554    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7919    1.2081   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -1.1144    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.0947   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7436    1.5540   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105    0.6087   -3.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772    0.7303   -3.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4177   -1.0084   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0516    0.6603   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    2.2355    0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    1.2846    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284    1.7953    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -0.7878    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -0.8303    2.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -1.8800    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055   -0.7557    1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7998    0.8388    1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2093    0.7962    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 25 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 29 60  1  0
M  CHG  2  24  -1  26   1
M  END


  Mrv1652303312121582D          

 29 28  0  0  0  0            999 V2000
    0.3316    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.1914    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    2.2539    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4586    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
M  CHG  2   3  -1  26   1
M  END
> <DATABASE_ID>
HMDB0241869

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H31N2O10P/c1-16(2,10-27-29(24,25)26)14(22)15(23)17-7-6-13(21)28-11(8-12(19)20)9-18(3,4)5/h11,14,22H,6-10H2,1-5H3,(H3-,17,19,20,23,24,25,26)

> <INCHI_KEY>
QFGWSPGUGXALMJ-UHFFFAOYSA-N

> <FORMULA>
C16H31N2O10P

> <MOLECULAR_WEIGHT>
442.402

> <EXACT_MASS>
442.171632204

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.4478619677226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <JCHEM_LOGP>
-5.701976061471745

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9533199612807075

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.790606374465587

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8105850508971644

> <JCHEM_POLAR_SURFACE_AREA>
182.51999999999998

> <JCHEM_REFRACTIVITY>
122.37709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241869
     RDKit          3D
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine
 60 59  0  0  0  0  0  0  0  0999 V2000
    6.0619   -1.5283    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653   -0.6502    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6065    0.2340    2.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2885    0.1255   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887    0.9639   -0.7179 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8723    1.7691   -2.0779 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.5425    3.2399   -1.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332    1.2084   -3.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5486    1.6436   -2.2087 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -1.6120    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -2.4080   -0.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.9447    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271   -1.1637   -0.9935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187   -0.0973    0.9928 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.5155    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311   -0.4492    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026    0.3141   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814    1.5652   -0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -0.3047   -0.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571    0.4609   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0600    0.1897   -2.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825   -1.2423   -3.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3975   -1.8163   -3.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -1.9930   -3.5474 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.2453    0.0659   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622    0.2199    0.6716 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.6565    1.4301    1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -0.8929    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6811    0.2570    1.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6787   -1.0127    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6940   -1.7212    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6662   -2.4382    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061    0.5490    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220    1.1883    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274   -0.3317    2.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482    0.7720    0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6628   -0.5772   -1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    1.1228   -4.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9319    2.0468   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -2.2710    1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608   -1.9205   -1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983    0.0976    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    1.1554    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7919    1.2081   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -1.1144    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.0947   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7436    1.5540   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105    0.6087   -3.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772    0.7303   -3.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4177   -1.0084   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0516    0.6603   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    2.2355    0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    1.2846    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284    1.7953    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -0.7878    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -0.8303    2.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -1.8800    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055   -0.7557    1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7998    0.8388    1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2093    0.7962    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 25 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 29 60  1  0
M  CHG  2  24  -1  26   1
M  END

HEADER    PROTEIN                                 31-MAR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-21         0                                  
HETATM    1  O   UNK     0       0.619   0.357   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.953   1.127   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.286   0.357   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.955   2.667   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.288   4.977   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.622   2.667   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.622   1.127   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.956   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.726   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.186   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.289   4.207   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.623   3.437   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      17.957   4.207   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      19.290   4.977   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.727   2.874   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      17.187   5.541   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.953   5.747   0.000  0.00  0.00           N+1
HETATM   27  C   UNK     0       2.723   7.081   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.183   4.414   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.619   6.517   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

COMPND    HMDB0241869
HETATM    1  C1  UNL     1       6.062  -1.528   1.365  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.865  -0.650   0.970  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.606   0.234   2.154  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.288   0.125  -0.255  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.289   0.964  -0.718  1.00  0.00           O  
HETATM    6  P1  UNL     1       4.872   1.769  -2.078  1.00  0.00           P  
HETATM    7  O2  UNL     1       4.542   3.240  -1.912  1.00  0.00           O  
HETATM    8  O3  UNL     1       4.133   1.208  -3.499  1.00  0.00           O  
HETATM    9  O4  UNL     1       6.549   1.644  -2.209  1.00  0.00           O  
HETATM   10  C5  UNL     1       3.740  -1.612   0.660  1.00  0.00           C  
HETATM   11  O5  UNL     1       4.214  -2.408  -0.389  1.00  0.00           O  
HETATM   12  C6  UNL     1       2.501  -0.945   0.203  1.00  0.00           C  
HETATM   13  O6  UNL     1       2.127  -1.164  -0.994  1.00  0.00           O  
HETATM   14  N1  UNL     1       1.719  -0.097   0.993  1.00  0.00           N  
HETATM   15  C7  UNL     1       0.524   0.515   0.483  1.00  0.00           C  
HETATM   16  C8  UNL     1      -0.531  -0.449   0.046  1.00  0.00           C  
HETATM   17  C9  UNL     1      -1.703   0.314  -0.453  1.00  0.00           C  
HETATM   18  O7  UNL     1      -1.681   1.565  -0.453  1.00  0.00           O  
HETATM   19  O8  UNL     1      -2.851  -0.305  -0.931  1.00  0.00           O  
HETATM   20  C10 UNL     1      -3.957   0.461  -1.402  1.00  0.00           C  
HETATM   21  C11 UNL     1      -4.060   0.190  -2.887  1.00  0.00           C  
HETATM   22  C12 UNL     1      -4.283  -1.242  -3.199  1.00  0.00           C  
HETATM   23  O9  UNL     1      -5.397  -1.816  -3.170  1.00  0.00           O  
HETATM   24  O10 UNL     1      -3.165  -1.993  -3.547  1.00  0.00           O1-
HETATM   25  C13 UNL     1      -5.245   0.066  -0.765  1.00  0.00           C  
HETATM   26  N2  UNL     1      -5.262   0.220   0.672  1.00  0.00           N1+
HETATM   27  C14 UNL     1      -4.656   1.430   1.131  1.00  0.00           C  
HETATM   28  C15 UNL     1      -4.680  -0.893   1.372  1.00  0.00           C  
HETATM   29  C16 UNL     1      -6.681   0.257   1.058  1.00  0.00           C  
HETATM   30  H1  UNL     1       6.679  -1.013   2.156  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.694  -1.721   0.488  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.666  -2.438   1.856  1.00  0.00           H  
HETATM   33  H4  UNL     1       5.606   0.549   2.584  1.00  0.00           H  
HETATM   34  H5  UNL     1       4.122   1.188   1.887  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.127  -0.332   2.959  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.148   0.772   0.074  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.663  -0.577  -1.012  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.836   1.123  -4.190  1.00  0.00           H  
HETATM   39  H10 UNL     1       6.932   2.047  -1.396  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.590  -2.271   1.532  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.961  -1.920  -1.232  1.00  0.00           H  
HETATM   42  H13 UNL     1       1.998   0.098   1.972  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.038   1.155   1.280  1.00  0.00           H  
HETATM   44  H15 UNL     1       0.792   1.208  -0.371  1.00  0.00           H  
HETATM   45  H16 UNL     1      -0.849  -1.114   0.893  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.161  -1.095  -0.767  1.00  0.00           H  
HETATM   47  H18 UNL     1      -3.744   1.554  -1.319  1.00  0.00           H  
HETATM   48  H19 UNL     1      -3.211   0.609  -3.452  1.00  0.00           H  
HETATM   49  H20 UNL     1      -4.977   0.730  -3.241  1.00  0.00           H  
HETATM   50  H21 UNL     1      -5.418  -1.008  -0.986  1.00  0.00           H  
HETATM   51  H22 UNL     1      -6.052   0.660  -1.223  1.00  0.00           H  
HETATM   52  H23 UNL     1      -4.728   2.236   0.376  1.00  0.00           H  
HETATM   53  H24 UNL     1      -3.617   1.285   1.495  1.00  0.00           H  
HETATM   54  H25 UNL     1      -5.228   1.795   2.017  1.00  0.00           H  
HETATM   55  H26 UNL     1      -3.582  -0.788   1.454  1.00  0.00           H  
HETATM   56  H27 UNL     1      -5.059  -0.830   2.432  1.00  0.00           H  
HETATM   57  H28 UNL     1      -4.991  -1.880   0.974  1.00  0.00           H  
HETATM   58  H29 UNL     1      -7.105  -0.756   1.108  1.00  0.00           H  
HETATM   59  H30 UNL     1      -6.800   0.839   1.995  1.00  0.00           H  
HETATM   60  H31 UNL     1      -7.209   0.796   0.247  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   10
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6
CONECT    6    7    7    8    9
CONECT    8   38
CONECT    9   39
CONECT   10   11   12   40
CONECT   11   41
CONECT   12   13   13   14
CONECT   14   15   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   25   47
CONECT   21   22   48   49
CONECT   22   23   23   24
CONECT   25   26   50   51
CONECT   26   27   28   29
CONECT   27   52   53   54
CONECT   28   55   56   57
CONECT   29   58   59   60
END

HMDB0241869
     RDKit          3D
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine
 60 59  0  0  0  0  0  0  0  0999 V2000
    6.0619   -1.5283    1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653   -0.6502    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6065    0.2340    2.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2885    0.1255   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887    0.9639   -0.7179 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8723    1.7691   -2.0779 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.5425    3.2399   -1.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332    1.2084   -3.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5486    1.6436   -2.2087 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -1.6120    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -2.4080   -0.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.9447    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1271   -1.1637   -0.9935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187   -0.0973    0.9928 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.5155    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311   -0.4492    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7026    0.3141   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814    1.5652   -0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -0.3047   -0.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571    0.4609   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0600    0.1897   -2.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825   -1.2423   -3.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3975   -1.8163   -3.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -1.9930   -3.5474 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.2453    0.0659   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622    0.2199    0.6716 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.6565    1.4301    1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -0.8929    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6811    0.2570    1.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6787   -1.0127    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6940   -1.7212    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6662   -2.4382    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061    0.5490    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220    1.1883    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274   -0.3317    2.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1482    0.7720    0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6628   -0.5772   -1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    1.1228   -4.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9319    2.0468   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -2.2710    1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9608   -1.9205   -1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983    0.0976    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384    1.1554    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7919    1.2081   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -1.1144    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.0947   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7436    1.5540   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105    0.6087   -3.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772    0.7303   -3.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4177   -1.0084   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0516    0.6603   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    2.2355    0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    1.2846    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284    1.7953    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -0.7878    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -0.8303    2.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -1.8800    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055   -0.7557    1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7998    0.8388    1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2093    0.7962    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 25 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 29 60  1  0
M  CHG  2  24  -1  26   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₃₁N₂O₁₀P

Average Molecular Weight

442.402

Monoisotopic Molecular Weight

442.171632204

IUPAC Name

3-[(3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C16H31N2O10P/c1-16(2,10-27-29(24,25)26)14(22)15(23)17-7-6-13(21)28-11(8-12(19)20)9-18(3,4)5/h11,14,22H,6-10H2,1-5H3,(H3-,17,19,20,23,24,25,26)

InChI Key

QFGWSPGUGXALMJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Beta amino acid or derivatives
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
N-acyl-amine
Monosaccharide
Fatty amide
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid salt
Carboxylic acid ester
Carboxamide group
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Not Available

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
logP	-5.7	ChemAxon
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	182.52 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	122.38 m³·mol⁻¹	ChemAxon
Polarizability	42.45 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M+H]+	214.985	30932474
DeepCCS	[M-H]-	212.627	30932474
DeepCCS	[M-2H]-	245.744	30932474
DeepCCS	[M+Na]+	221.079	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.643 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	472.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	182.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	105.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	254.8 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	319.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	912.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	92.1 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	859.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	522.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	377.6 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	221.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine	CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	3426.8	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine	CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2242.1	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine	CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	3056.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,1TMS,isomer #1	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2927.2	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,1TMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2975.8	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,1TMS,isomer #3	CC(C)(COP(=O)(O)O)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2962.8	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #1	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2885.4	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #1	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2885.8	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #1	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3698.5	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #2	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2934.6	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #2	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2921.9	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #2	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	3908.7	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2936.9	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2916.3	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3688.5	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #4	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2907.4	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #4	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2919.2	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TMS,isomer #4	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	3856.0	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2862.2	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2911.1	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3311.9	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2889.9	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2920.5	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	3483.4	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2886.9	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2938.3	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	3499.4	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,4TMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2882.6	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,4TMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	2924.3	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,4TMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C	3185.8	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,1TBDMS,isomer #1	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3130.9	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,1TBDMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3194.4	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,1TBDMS,isomer #3	CC(C)(COP(=O)(O)O)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3178.9	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #1	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3310.3	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #1	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3245.2	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #1	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3732.1	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #2	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3363.1	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #2	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3303.7	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #2	CC(C)(COP(=O)(O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3917.5	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3397.1	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3247.4	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3759.1	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #4	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3373.1	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #4	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3279.6	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,2TBDMS,isomer #4	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3900.3	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3509.3	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3382.4	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)NCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C	3456.2	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3534.4	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3438.7	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #2	CC(C)(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3598.0	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3545.3	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3423.2	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,3TBDMS,isomer #3	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3623.2	Standard polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,4TBDMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3702.3	Semi standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,4TBDMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3563.0	Standard non polar	33892256
3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine,4TBDMS,isomer #1	CC(C)(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)N(CCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)[Si](C)(C)C(C)(C)C	3437.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 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 - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 10V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 20V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 40V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 10V, Positive-QTOF	splash10-0006-0000900000-68a6404f5c5a61c965b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 20V, Positive-QTOF	splash10-000l-9000500000-352e888cc989bd3350ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Acylcarnitine 3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156962954

PDB ID

Not Available

ChEBI ID

Not Available

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

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for 3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine (HMDB0241869)

MOL for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

3D MOL for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

3D SDF for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

3D-SDF for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

PDB for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

3D PDB for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

SMILES for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

INCHI for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

Structure for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

3D Structure for HMDB0241869 (3-[(2R)-2-Hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanoylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra