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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-04-11 22:16:19 UTC

Update Date

2022-10-24 19:44:14 UTC

HMDB ID

HMDB0061639

Secondary Accession Numbers

HMDB61639

Metabolite Identification

Common Name

3-hydroxytridecanoyl carnitine

Description

3-Hydroxytridecanoyl carnitine is an acylcarnitine. More specifically, it is an 3-hydroxytridecanoic 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-Hydroxytridecanoyl carnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 3-hydroxytridecanoyl carnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). 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

3-hydroxytridecanoyl carnitine
  Mrv0541 04111415162D          

 26 25  0  0  0  0            999 V2000
    5.9961    2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    3.4618    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.8211    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816    5.5243    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.9961    6.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  CHG  2   2   1  25  -1
M  END

HMDB0061639
     RDKit          3D
3-hydroxytridecanoyl carnitine
 65 64  0  0  0  0  0  0  0  0999 V2000
    9.7807   -0.0056   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6121   -0.7717    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3076   -1.4338    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0955   -0.5921    0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734    0.2571   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676    1.0300   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2895    0.1415   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0880    1.0586    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.2402    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    1.1948    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    0.4152    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -0.3809   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    1.4061    0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    0.6972    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.3800    2.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762    0.3925    0.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.2849    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0164   -1.6432   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109   -1.6217   -1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -0.5570   -2.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829   -2.8052   -2.5803 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.2370    0.5680   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5631    0.0668   -0.1979 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.9828   -0.7328   -1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4349    1.2638   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8849   -0.6093    1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820   -0.2595   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8311    1.0962   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0302   -0.3088   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864   -0.1015    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089   -1.5574    0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3457   -2.0727    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -2.2164   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2246   -1.2610    0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1852    0.0975    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6375   -0.3098   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5226    1.1038   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    1.6684   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6329    1.6848    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -0.4329   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664   -0.5679    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3118    1.6262    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958    1.7336   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -0.3919    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -0.3726   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    1.8189   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    1.8378    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4690   -0.1716    1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -1.2842   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    2.1363    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    1.9733   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764   -0.4641    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384   -2.1782    0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8731   -2.3067   -0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1971    1.5204    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0518    0.8082   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0218   -1.8233   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0153   -0.4469   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3539   -0.4774   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9285    1.9818    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3974    1.6421   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4365    0.9891    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7047   -1.3361    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3032    0.0943    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0767   -1.1452    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  CHG  2  21  -1  23   1
M  END

3-hydroxytridecanoyl carnitine
  Mrv0541 04111415162D          

 26 25  0  0  0  0            999 V2000
    5.9961    2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    3.4618    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.8211    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816    5.5243    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.9961    6.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  CHG  2   2   1  25  -1
M  END
> <DATABASE_ID>
HMDB0061639

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H39NO5/c1-5-6-7-8-9-10-11-12-13-17(22)14-20(25)26-18(15-19(23)24)16-21(2,3)4/h17-18,22H,5-16H2,1-4H3

> <INCHI_KEY>
DOFFCMLMRQLXPK-UHFFFAOYSA-N

> <FORMULA>
C20H39NO5

> <MOLECULAR_WEIGHT>
373.5274

> <EXACT_MASS>
373.282823363

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.11086815974937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-0.97

> <JCHEM_LOGP>
-0.5309692078050805

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.000091801572765

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.102434316471337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798760130283852

> <JCHEM_POLAR_SURFACE_AREA>
86.66

> <JCHEM_REFRACTIVITY>
124.7892

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3-hydroxytridecanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061639
     RDKit          3D
3-hydroxytridecanoyl carnitine
 65 64  0  0  0  0  0  0  0  0999 V2000
    9.7807   -0.0056   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6121   -0.7717    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3076   -1.4338    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0955   -0.5921    0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734    0.2571   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676    1.0300   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2895    0.1415   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0880    1.0586    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.2402    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    1.1948    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    0.4152    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -0.3809   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    1.4061    0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    0.6972    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.3800    2.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762    0.3925    0.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.2849    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0164   -1.6432   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109   -1.6217   -1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -0.5570   -2.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829   -2.8052   -2.5803 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.2370    0.5680   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5631    0.0668   -0.1979 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.9828   -0.7328   -1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4349    1.2638   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8849   -0.6093    1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820   -0.2595   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8311    1.0962   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0302   -0.3088   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864   -0.1015    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089   -1.5574    0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3457   -2.0727    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -2.2164   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2246   -1.2610    0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1852    0.0975    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6375   -0.3098   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5226    1.1038   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    1.6684   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6329    1.6848    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -0.4329   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664   -0.5679    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3118    1.6262    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958    1.7336   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -0.3919    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -0.3726   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    1.8189   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    1.8378    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4690   -0.1716    1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -1.2842   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    2.1363    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    1.9733   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764   -0.4641    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384   -2.1782    0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8731   -2.3067   -0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1971    1.5204    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0518    0.8082   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0218   -1.8233   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0153   -0.4469   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3539   -0.4774   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9285    1.9818    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3974    1.6421   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4365    0.9891    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7047   -1.3361    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3032    0.0943    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0767   -1.1452    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  CHG  2  21  -1  23   1
M  END

HEADER    PROTEIN                                 11-APR-14   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-hydroxytridecanoyl carnitine                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-APR-14         0                                  
HETATM    1  C   UNK     0      11.193   4.922   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      11.193   6.462   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      12.733   6.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.653   6.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.193   8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.860   8.002   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.194  10.312   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.861  10.312   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.531   8.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.198   8.772   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.526  10.312   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.193  11.082   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.859  10.312   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      11.193  12.622   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    6   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0061639
HETATM    1  C1  UNL     1       9.781  -0.006  -1.069  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.612  -0.772   0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.308  -1.434   0.421  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.095  -0.592   0.520  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.773   0.257  -0.649  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.468   1.030  -0.402  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.290   0.141  -0.180  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.088   1.059   0.033  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.853   0.240   0.264  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.690   1.195   0.468  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.567   0.415   0.701  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.779  -0.381  -0.431  1.00  0.00           O  
HETATM   13  C12 UNL     1      -1.710   1.406   0.780  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.008   0.697   1.013  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.294   0.380   2.176  1.00  0.00           O  
HETATM   16  O3  UNL     1      -3.876   0.393   0.004  1.00  0.00           O  
HETATM   17  C14 UNL     1      -5.130  -0.285   0.182  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.016  -1.643  -0.433  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.711  -1.622  -1.874  1.00  0.00           C  
HETATM   20  O4  UNL     1      -4.556  -0.557  -2.517  1.00  0.00           O  
HETATM   21  O5  UNL     1      -4.583  -2.805  -2.580  1.00  0.00           O1-
HETATM   22  C17 UNL     1      -6.237   0.568  -0.293  1.00  0.00           C  
HETATM   23  N1  UNL     1      -7.563   0.067  -0.198  1.00  0.00           N1+
HETATM   24  C18 UNL     1      -7.983  -0.733  -1.305  1.00  0.00           C  
HETATM   25  C19 UNL     1      -8.435   1.264  -0.193  1.00  0.00           C  
HETATM   26  C20 UNL     1      -7.885  -0.609   1.037  1.00  0.00           C  
HETATM   27  H1  UNL     1      10.782  -0.260  -1.529  1.00  0.00           H  
HETATM   28  H2  UNL     1       9.831   1.096  -0.931  1.00  0.00           H  
HETATM   29  H3  UNL     1       9.030  -0.309  -1.807  1.00  0.00           H  
HETATM   30  H4  UNL     1       9.886  -0.102   1.078  1.00  0.00           H  
HETATM   31  H5  UNL     1      10.409  -1.557   0.241  1.00  0.00           H  
HETATM   32  H6  UNL     1       8.346  -2.073   1.357  1.00  0.00           H  
HETATM   33  H7  UNL     1       8.125  -2.216  -0.385  1.00  0.00           H  
HETATM   34  H8  UNL     1       6.225  -1.261   0.747  1.00  0.00           H  
HETATM   35  H9  UNL     1       7.185   0.098   1.420  1.00  0.00           H  
HETATM   36  H10 UNL     1       6.637  -0.310  -1.568  1.00  0.00           H  
HETATM   37  H11 UNL     1       7.523   1.104  -0.753  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.265   1.668  -1.282  1.00  0.00           H  
HETATM   39  H13 UNL     1       5.633   1.685   0.477  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.062  -0.433  -1.107  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.366  -0.568   0.648  1.00  0.00           H  
HETATM   42  H16 UNL     1       3.312   1.626   0.975  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.996   1.734  -0.819  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.008  -0.392   1.155  1.00  0.00           H  
HETATM   45  H19 UNL     1       1.659  -0.373  -0.638  1.00  0.00           H  
HETATM   46  H20 UNL     1       0.612   1.819  -0.428  1.00  0.00           H  
HETATM   47  H21 UNL     1       0.914   1.838   1.361  1.00  0.00           H  
HETATM   48  H22 UNL     1      -0.469  -0.172   1.630  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.029  -1.284  -0.097  1.00  0.00           H  
HETATM   50  H24 UNL     1      -1.502   2.136   1.602  1.00  0.00           H  
HETATM   51  H25 UNL     1      -1.756   1.973  -0.157  1.00  0.00           H  
HETATM   52  H26 UNL     1      -5.176  -0.464   1.298  1.00  0.00           H  
HETATM   53  H27 UNL     1      -4.138  -2.178   0.045  1.00  0.00           H  
HETATM   54  H28 UNL     1      -5.873  -2.307  -0.195  1.00  0.00           H  
HETATM   55  H29 UNL     1      -6.197   1.520   0.318  1.00  0.00           H  
HETATM   56  H30 UNL     1      -6.052   0.808  -1.370  1.00  0.00           H  
HETATM   57  H31 UNL     1      -8.022  -1.823  -1.107  1.00  0.00           H  
HETATM   58  H32 UNL     1      -9.015  -0.447  -1.588  1.00  0.00           H  
HETATM   59  H33 UNL     1      -7.354  -0.477  -2.191  1.00  0.00           H  
HETATM   60  H34 UNL     1      -7.928   1.982   0.487  1.00  0.00           H  
HETATM   61  H35 UNL     1      -8.397   1.642  -1.234  1.00  0.00           H  
HETATM   62  H36 UNL     1      -9.436   0.989   0.148  1.00  0.00           H  
HETATM   63  H37 UNL     1      -8.705  -1.336   0.819  1.00  0.00           H  
HETATM   64  H38 UNL     1      -8.303   0.094   1.813  1.00  0.00           H  
HETATM   65  H39 UNL     1      -7.077  -1.145   1.517  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   13   48
CONECT   12   49
CONECT   13   14   50   51
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   22   52
CONECT   18   19   53   54
CONECT   19   20   20   21
CONECT   22   23   55   56
CONECT   23   24   25   26
CONECT   24   57   58   59
CONECT   25   60   61   62
CONECT   26   63   64   65
END

HMDB0061639
     RDKit          3D
3-hydroxytridecanoyl carnitine
 65 64  0  0  0  0  0  0  0  0999 V2000
    9.7807   -0.0056   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6121   -0.7717    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3076   -1.4338    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0955   -0.5921    0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7734    0.2571   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676    1.0300   -0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2895    0.1415   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0880    1.0586    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.2402    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    1.1948    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    0.4152    0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -0.3809   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    1.4061    0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    0.6972    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.3800    2.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762    0.3925    0.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.2849    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0164   -1.6432   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109   -1.6217   -1.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -0.5570   -2.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829   -2.8052   -2.5803 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.2370    0.5680   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5631    0.0668   -0.1979 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.9828   -0.7328   -1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4349    1.2638   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8849   -0.6093    1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820   -0.2595   -1.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8311    1.0962   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0302   -0.3088   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864   -0.1015    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089   -1.5574    0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3457   -2.0727    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -2.2164   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2246   -1.2610    0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1852    0.0975    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6375   -0.3098   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5226    1.1038   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    1.6684   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6329    1.6848    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -0.4329   -1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3664   -0.5679    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3118    1.6262    0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958    1.7336   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -0.3919    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6594   -0.3726   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116    1.8189   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    1.8378    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4690   -0.1716    1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -1.2842   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    2.1363    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    1.9733   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764   -0.4641    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384   -2.1782    0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8731   -2.3067   -0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1971    1.5204    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0518    0.8082   -1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0218   -1.8233   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0153   -0.4469   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3539   -0.4774   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9285    1.9818    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3974    1.6421   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4365    0.9891    0.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7047   -1.3361    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3032    0.0943    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0767   -1.1452    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  CHG  2  21  -1  23   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₃₉NO₅

Average Molecular Weight

373.5274

Monoisotopic Molecular Weight

373.282823363

IUPAC Name

3-[(3-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(3-hydroxytridecanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H39NO5/c1-5-6-7-8-9-10-11-12-13-17(22)14-20(25)26-18(15-19(23)24)16-21(2,3)4/h17-18,22H,5-16H2,1-4H3

InChI Key

DOFFCMLMRQLXPK-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-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

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

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0061639)

Endogenous

Endogenous (HMDB: HMDB0061639)

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
Water Solubility	0.00059 g/L	ALOGPS
logP	-0.97	ALOGPS
logP	-0.53	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	124.79 m³·mol⁻¹	ChemAxon
Polarizability	44.11 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]+	207.289	30932474
DeepCCS	[M-H]-	203.269	30932474
DeepCCS	[M-2H]-	239.813	30932474
DeepCCS	[M+Na]+	216.104	30932474
AllCCS	[M+H]+	204.8	32859911
AllCCS	[M+H-H2O]+	202.6	32859911
AllCCS	[M+NH4]+	206.7	32859911
AllCCS	[M+Na]+	207.3	32859911
AllCCS	[M-H]-	201.5	32859911
AllCCS	[M+Na-2H]-	202.8	32859911
AllCCS	[M+HCOO]-	204.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-hydroxytridecanoyl carnitine	CCCCCCCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	3139.9	Standard polar	33892256
3-hydroxytridecanoyl carnitine	CCCCCCCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2302.4	Standard non polar	33892256
3-hydroxytridecanoyl carnitine	CCCCCCCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2524.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-hydroxytridecanoyl carnitine,1TMS,isomer #1	CCCCCCCCCCC(CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	2499.9	Semi standard non polar	33892256
3-hydroxytridecanoyl carnitine,1TBDMS,isomer #1	CCCCCCCCCCC(CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	2724.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-hydroxytridecanoyl carnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9310000000-12f87eb4bd8f2df3a4dd	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-hydroxytridecanoyl carnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9120000000-f1e7d5bac88607585b0e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-hydroxytridecanoyl carnitine 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-hydroxytridecanoyl carnitine 10V, Positive-QTOF	splash10-0c03-0719000000-f70584927920b08384b2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 20V, Positive-QTOF	splash10-0006-1901000000-91300e02ff2260857fda	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 40V, Positive-QTOF	splash10-0006-5900000000-722f0c77131aeb94d70e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 10V, Negative-QTOF	splash10-00di-1029000000-3e65b1ea118b09c28aca	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 20V, Negative-QTOF	splash10-044i-1889000000-0cdf18619247b94246cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 40V, Negative-QTOF	splash10-01rf-6960000000-725d10155b94a064c455	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 20V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 10V, Positive-QTOF	splash10-00di-0009000000-8245c57c5e589666494e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 20V, Positive-QTOF	splash10-0079-9005000000-a1d4b2a6211734d00eb6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxytridecanoyl carnitine 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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

131770392

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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 ]
Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931. [PubMed:22804748 ]
Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
The AOCS Lipid Library [Link]

Showing metabocard for 3-hydroxytridecanoyl carnitine (HMDB0061639)

MOL for HMDB0061639 (3-hydroxytridecanoyl carnitine)

3D MOL for HMDB0061639 (3-hydroxytridecanoyl carnitine)

3D SDF for HMDB0061639 (3-hydroxytridecanoyl carnitine)

3D-SDF for HMDB0061639 (3-hydroxytridecanoyl carnitine)

PDB for HMDB0061639 (3-hydroxytridecanoyl carnitine)

3D PDB for HMDB0061639 (3-hydroxytridecanoyl carnitine)

SMILES for HMDB0061639 (3-hydroxytridecanoyl carnitine)

INCHI for HMDB0061639 (3-hydroxytridecanoyl carnitine)

Structure for HMDB0061639 (3-hydroxytridecanoyl carnitine)

3D Structure for HMDB0061639 (3-hydroxytridecanoyl carnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra