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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-23 13:06:02 UTC

Update Date

2022-10-24 19:44:11 UTC

HMDB ID

HMDB0005065

Secondary Accession Numbers

HMDB0062772
HMDB05065
HMDB62772

Metabolite Identification

Common Name

Oleoylcarnitine

Description

Oleoylcarnitine is an acylcarnitine. More specifically, it is an oleic 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. Oleoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine oleoylcarnitine 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. In particular oleoylcarnitine is elevated in the blood or plasma of individuals with carnitine palmitoyl transferase 2 deficiency (PMID: 15653102 , PMID: 11999976 ), cardiovascular mortality in incident dialysis patients (PMID: 24308938 ), schizophrenia (PMID: 31161852 ), succinic semialdehyde dehydrogenase deficiency (PMID: 32967698 ), neonatal macrosomia (PMID: 32126138 ), liver cirrhosis (PMID: 32075591 ), CPT II deficiency (PMID: 28801073 , PMID: 18987586 , PMID: 18925671 , PMID: 11585077 ), carnitine/acylcarnitine translocase (CACT) deficiency (PMID: 15057979 ), and ischaemia/reperfusion (PMID: 26936967 , PMID: 22607863 , PMID: 24468136 ). 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

  Mrv1652311291719522D          

 30 29  0  0  0  0            999 V2000
 2493.9443 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2494.6583 2499.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0863 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5143 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2283 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9423 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6564 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3702 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0842 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9087 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.6227 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.3388 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.0528 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.7668 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.4808 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.1946 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.9086 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2507.6226 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2500.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9443 2500.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.0361    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2492.5122 2500.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2492.3773 2501.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2499.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2498.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9526 2498.1392    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2492.5246 2498.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  6  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  CHG  2  23   1  29  -1
M  END

HMDB0005065
     RDKit          3D
Oleoylcarnitine
 78 77  0  0  0  0  0  0  0  0999 V2000
   11.2633   -1.0946   -1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8186   -0.6556   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1700   -1.1396    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473   -0.6509    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -1.0577    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5739   -0.5053    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882   -0.8443    2.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -0.2217    2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358    1.2337    1.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457    1.9272    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.2996   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.8947   -0.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    1.2441   -1.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    1.7449   -2.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    1.4971   -1.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8526    0.0586   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -0.1244    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2196    0.3446   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    0.7465   -1.6090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3487    0.3709    0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6054    0.8115   -0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9471    2.0920    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093    1.9173    2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3371    2.9102    2.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7323    0.7387    2.8208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6257   -0.2457    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3242   -1.4644   -0.5739 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.5069   -2.3477   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0085   -1.2865   -1.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297   -2.2032    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5388   -1.6433   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9523   -0.2334   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3499   -1.7188   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2009   -1.0361   -1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8051    0.4463   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7069   -0.6391    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2806   -2.2140    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889    0.4728    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -0.9618   -0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4520   -0.6823    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221   -2.1766    1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1347   -0.8717    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836    0.6095    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0727   -0.4551    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362   -1.9368    2.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.7602    1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7297   -0.3880    2.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076    1.7835    2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761    3.0009    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321    0.2166   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509    1.6166   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934    1.6909    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.9907   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388    1.4681   -2.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900    0.1492   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    1.3793   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5212    2.8631   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386    2.0325   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.9317   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.4127   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -0.5279   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6293    0.4135    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -1.2124    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5613    1.0939   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9155    2.4887    0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1887    2.8657    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4364    0.6741    3.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6243    0.0924   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8082   -0.5054    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1571   -3.3858   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0480   -2.1223    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1737   -2.1502   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2536   -0.3195   -2.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5584   -2.0541   -2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9227   -1.4895   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5308   -3.2724    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9316   -1.7941    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3534   -2.3061   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 21 64  1  6
 22 65  1  0
 22 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  CHG  1  27   1
M  END

  Mrv1652311291719522D          

 30 29  0  0  0  0            999 V2000
 2493.9443 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2494.6583 2499.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0863 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5143 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2283 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9423 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6564 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3702 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0842 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.9087 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.6227 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.3388 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.0528 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.7668 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.4808 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.1946 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2506.9086 2499.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2507.6226 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2500.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9443 2500.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.0361    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2492.5122 2500.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2492.3773 2501.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2499.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2498.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9526 2498.1392    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2492.5246 2498.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  6  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  CHG  2  23   1  29  -1
M  END
> <DATABASE_ID>
HMDB0005065

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h12-13,23H,5-11,14-22H2,1-4H3/b13-12-/t23-/m1/s1

> <INCHI_KEY>
IPOLTUVFXFHAHI-WHIOSMTNSA-N

> <FORMULA>
C25H47NO4

> <MOLECULAR_WEIGHT>
425.654

> <EXACT_MASS>
425.350508997

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.06792359615166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.5607635275282545

> <ALOGPS_LOGS>
-7.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0571868920224

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
147.39530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005065
     RDKit          3D
Oleoylcarnitine
 78 77  0  0  0  0  0  0  0  0999 V2000
   11.2633   -1.0946   -1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8186   -0.6556   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1700   -1.1396    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473   -0.6509    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -1.0577    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5739   -0.5053    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882   -0.8443    2.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -0.2217    2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358    1.2337    1.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457    1.9272    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.2996   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.8947   -0.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    1.2441   -1.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    1.7449   -2.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    1.4971   -1.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8526    0.0586   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -0.1244    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2196    0.3446   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    0.7465   -1.6090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3487    0.3709    0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6054    0.8115   -0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9471    2.0920    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093    1.9173    2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3371    2.9102    2.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7323    0.7387    2.8208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6257   -0.2457    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3242   -1.4644   -0.5739 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.5069   -2.3477   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0085   -1.2865   -1.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297   -2.2032    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5388   -1.6433   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9523   -0.2334   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3499   -1.7188   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2009   -1.0361   -1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8051    0.4463   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7069   -0.6391    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2806   -2.2140    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889    0.4728    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -0.9618   -0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4520   -0.6823    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221   -2.1766    1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1347   -0.8717    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836    0.6095    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0727   -0.4551    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362   -1.9368    2.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.7602    1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7297   -0.3880    2.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076    1.7835    2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761    3.0009    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321    0.2166   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509    1.6166   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934    1.6909    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.9907   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388    1.4681   -2.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900    0.1492   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    1.3793   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5212    2.8631   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386    2.0325   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.9317   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.4127   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -0.5279   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6293    0.4135    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -1.2124    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5613    1.0939   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9155    2.4887    0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1887    2.8657    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4364    0.6741    3.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6243    0.0924   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8082   -0.5054    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1571   -3.3858   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0480   -2.1223    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1737   -2.1502   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2536   -0.3195   -2.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5584   -2.0541   -2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9227   -1.4895   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5308   -3.2724    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9316   -1.7941    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3534   -2.3061   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 21 64  1  6
 22 65  1  0
 22 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  CHG  1  27   1
M  END

HEADER    PROTEIN                                 29-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-NOV-17         0                                  
HETATM    1  C   UNK     0    4655.3634666.294   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4656.6954665.523   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4658.0284666.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4659.3614665.523   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4660.6944666.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4662.0274665.523   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4663.3594666.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4664.6924665.523   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4666.0254666.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4667.3584665.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4668.6914666.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4670.2304666.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4671.5624665.523   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4672.8994666.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4674.2324665.523   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4675.5654666.294   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4676.8974665.523   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4678.2304666.294   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4679.5634665.523   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4680.8964666.294   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    4658.0284667.833   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    4655.3634667.833   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0    4654.0304668.601   0.000  0.00  0.00           N+1
HETATM   24  C   UNK     0    4652.6894667.830   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    4654.0304670.140   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4652.4384669.521   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4654.0414665.504   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    4654.0414663.965   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    4655.3784663.193   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0    4652.7134663.193   0.000  0.00  0.00           O+0
CONECT    1    2   22   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    3                                                            
CONECT   22    1   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27    1   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0005065
HETATM    1  C1  UNL     1      11.263  -1.095  -1.247  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.819  -0.656  -1.166  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.170  -1.140   0.136  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.747  -0.651   0.110  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.976  -1.058   1.345  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.574  -0.505   1.183  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.688  -0.844   2.359  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.320  -0.222   2.041  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.436   1.234   1.882  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.146   1.927   0.817  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.643   1.300  -0.413  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.258   1.895  -0.701  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.747   1.244  -1.965  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.602   1.745  -2.349  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.666   1.497  -1.300  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.853   0.059  -0.987  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.912  -0.124   0.055  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.220   0.345  -0.443  1.00  0.00           C  
HETATM   19  O1  UNL     1      -4.456   0.747  -1.609  1.00  0.00           O  
HETATM   20  O2  UNL     1      -5.349   0.371   0.409  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.605   0.811  -0.047  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.947   2.092   0.702  1.00  0.00           C  
HETATM   23  C21 UNL     1      -7.009   1.917   2.158  1.00  0.00           C  
HETATM   24  O3  UNL     1      -7.337   2.910   2.854  1.00  0.00           O  
HETATM   25  O4  UNL     1      -6.732   0.739   2.821  1.00  0.00           O  
HETATM   26  C22 UNL     1      -7.626  -0.246   0.133  1.00  0.00           C  
HETATM   27  N1  UNL     1      -7.324  -1.464  -0.574  1.00  0.00           N1+
HETATM   28  C23 UNL     1      -8.507  -2.348  -0.476  1.00  0.00           C  
HETATM   29  C24 UNL     1      -7.008  -1.287  -1.959  1.00  0.00           C  
HETATM   30  C25 UNL     1      -6.230  -2.203   0.062  1.00  0.00           C  
HETATM   31  H1  UNL     1      11.539  -1.643  -0.330  1.00  0.00           H  
HETATM   32  H2  UNL     1      11.952  -0.233  -1.335  1.00  0.00           H  
HETATM   33  H3  UNL     1      11.350  -1.719  -2.160  1.00  0.00           H  
HETATM   34  H4  UNL     1       9.201  -1.036  -1.988  1.00  0.00           H  
HETATM   35  H5  UNL     1       9.805   0.446  -1.224  1.00  0.00           H  
HETATM   36  H6  UNL     1       9.707  -0.639   0.958  1.00  0.00           H  
HETATM   37  H7  UNL     1       9.281  -2.214   0.267  1.00  0.00           H  
HETATM   38  H8  UNL     1       7.789   0.473   0.126  1.00  0.00           H  
HETATM   39  H9  UNL     1       7.193  -0.962  -0.780  1.00  0.00           H  
HETATM   40  H10 UNL     1       7.452  -0.682   2.273  1.00  0.00           H  
HETATM   41  H11 UNL     1       6.922  -2.177   1.320  1.00  0.00           H  
HETATM   42  H12 UNL     1       5.135  -0.872   0.257  1.00  0.00           H  
HETATM   43  H13 UNL     1       5.684   0.610   1.167  1.00  0.00           H  
HETATM   44  H14 UNL     1       5.073  -0.455   3.304  1.00  0.00           H  
HETATM   45  H15 UNL     1       4.536  -1.937   2.440  1.00  0.00           H  
HETATM   46  H16 UNL     1       2.788  -0.760   1.268  1.00  0.00           H  
HETATM   47  H17 UNL     1       2.730  -0.388   2.991  1.00  0.00           H  
HETATM   48  H18 UNL     1       3.808   1.783   2.761  1.00  0.00           H  
HETATM   49  H19 UNL     1       3.276   3.001   0.829  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.632   0.217  -0.447  1.00  0.00           H  
HETATM   51  H21 UNL     1       3.251   1.617  -1.318  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.593   1.691   0.154  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.352   2.991  -0.815  1.00  0.00           H  
HETATM   54  H24 UNL     1       1.439   1.468  -2.803  1.00  0.00           H  
HETATM   55  H25 UNL     1       0.790   0.149  -1.811  1.00  0.00           H  
HETATM   56  H26 UNL     1      -0.891   1.379  -3.336  1.00  0.00           H  
HETATM   57  H27 UNL     1      -0.521   2.863  -2.439  1.00  0.00           H  
HETATM   58  H28 UNL     1      -1.439   2.032  -0.354  1.00  0.00           H  
HETATM   59  H29 UNL     1      -2.591   1.932  -1.694  1.00  0.00           H  
HETATM   60  H30 UNL     1      -0.901  -0.413  -0.593  1.00  0.00           H  
HETATM   61  H31 UNL     1      -2.202  -0.528  -1.883  1.00  0.00           H  
HETATM   62  H32 UNL     1      -2.629   0.413   1.012  1.00  0.00           H  
HETATM   63  H33 UNL     1      -3.043  -1.212   0.299  1.00  0.00           H  
HETATM   64  H34 UNL     1      -6.561   1.094  -1.140  1.00  0.00           H  
HETATM   65  H35 UNL     1      -7.916   2.489   0.278  1.00  0.00           H  
HETATM   66  H36 UNL     1      -6.189   2.866   0.469  1.00  0.00           H  
HETATM   67  H37 UNL     1      -6.436   0.674   3.772  1.00  0.00           H  
HETATM   68  H38 UNL     1      -8.624   0.092  -0.275  1.00  0.00           H  
HETATM   69  H39 UNL     1      -7.808  -0.505   1.197  1.00  0.00           H  
HETATM   70  H40 UNL     1      -8.157  -3.386  -0.440  1.00  0.00           H  
HETATM   71  H41 UNL     1      -9.048  -2.122   0.457  1.00  0.00           H  
HETATM   72  H42 UNL     1      -9.174  -2.150  -1.349  1.00  0.00           H  
HETATM   73  H43 UNL     1      -7.254  -0.320  -2.394  1.00  0.00           H  
HETATM   74  H44 UNL     1      -7.558  -2.054  -2.583  1.00  0.00           H  
HETATM   75  H45 UNL     1      -5.923  -1.490  -2.175  1.00  0.00           H  
HETATM   76  H46 UNL     1      -6.531  -3.272   0.272  1.00  0.00           H  
HETATM   77  H47 UNL     1      -5.932  -1.794   1.027  1.00  0.00           H  
HETATM   78  H48 UNL     1      -5.353  -2.306  -0.623  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6   40   41
CONECT    6    7   42   43
CONECT    7    8   44   45
CONECT    8    9   46   47
CONECT    9   10   10   48
CONECT   10   11   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   54   55
CONECT   14   15   56   57
CONECT   15   16   58   59
CONECT   16   17   60   61
CONECT   17   18   62   63
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   26   64
CONECT   22   23   65   66
CONECT   23   24   24   25
CONECT   25   67
CONECT   26   27   68   69
CONECT   27   28   29   30
CONECT   28   70   71   72
CONECT   29   73   74   75
CONECT   30   76   77   78
END

HMDB0005065
     RDKit          3D
Oleoylcarnitine
 78 77  0  0  0  0  0  0  0  0999 V2000
   11.2633   -1.0946   -1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8186   -0.6556   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1700   -1.1396    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473   -0.6509    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -1.0577    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5739   -0.5053    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6882   -0.8443    2.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -0.2217    2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358    1.2337    1.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1457    1.9272    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.2996   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.8947   -0.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7474    1.2441   -1.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    1.7449   -2.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    1.4971   -1.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8526    0.0586   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9123   -0.1244    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2196    0.3446   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    0.7465   -1.6090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3487    0.3709    0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6054    0.8115   -0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9471    2.0920    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0093    1.9173    2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3371    2.9102    2.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7323    0.7387    2.8208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6257   -0.2457    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3242   -1.4644   -0.5739 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.5069   -2.3477   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0085   -1.2865   -1.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297   -2.2032    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5388   -1.6433   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9523   -0.2334   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3499   -1.7188   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2009   -1.0361   -1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8051    0.4463   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7069   -0.6391    0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2806   -2.2140    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7889    0.4728    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1930   -0.9618   -0.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4520   -0.6823    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221   -2.1766    1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1347   -0.8717    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836    0.6095    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0727   -0.4551    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362   -1.9368    2.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.7602    1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7297   -0.3880    2.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076    1.7835    2.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761    3.0009    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321    0.2166   -0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509    1.6166   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934    1.6909    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.9907   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388    1.4681   -2.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900    0.1492   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    1.3793   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5212    2.8631   -2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386    2.0325   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    1.9317   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.4127   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -0.5279   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6293    0.4135    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -1.2124    0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5613    1.0939   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9155    2.4887    0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1887    2.8657    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4364    0.6741    3.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6243    0.0924   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8082   -0.5054    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1571   -3.3858   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0480   -2.1223    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1737   -2.1502   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2536   -0.3195   -2.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5584   -2.0541   -2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9227   -1.4895   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5308   -3.2724    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9316   -1.7941    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3534   -2.3061   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 21 64  1  6
 22 65  1  0
 22 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  CHG  1  27   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z)-Octadecenoyl-L-carnitine	ChEBI
(R)-[(9Z)-Octadecenoyl]carnitine	ChEBI
Acylcarnitine C18:1	ChEBI
O-(9Z)-Octadecenoyl-(R)-carnitine	ChEBI
Oleoyl-L-carnitine	ChEBI
(Z)-(+-)-3-Carboxy-N,N,N-trimethyl-2-((1-oxo-9-octadecenyl)oxy)-1-propanaminium	HMDB
Oleoylcarnitine, (R-(Z))-isomer	HMDB
O-Oleoylcarnitine	HMDB
(9Z)-Octadec-9-enoylcarnitine	HMDB
cis-9-Octadecenoylcarnitine	HMDB
(R)-Oleoylcarnitine	HMDB
Oleoylcarnitine	ChEBI

Chemical Formula

C₂₅H₄₈NO₄

Average Molecular Weight

426.661

Monoisotopic Molecular Weight

426.35778545

IUPAC Name

(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

38677-66-6

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h12-13,23H,5-11,14-22H2,1-4H3/p+1/b13-12-/t23-/m1/s1

InChI Key

IPOLTUVFXFHAHI-WHIOSMTNSA-O

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
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:84651 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 25754623)

Organ

Placenta (HMDB: HMDB0005065)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (PMID: 32966057)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0005065)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0005065)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.7e-06 g/L	ALOGPS
logP	2.02	ALOGPS
logP	2.56	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	147.4 m³·mol⁻¹	ChemAxon
Polarizability	53.07 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]+	221.957	30932474
DeepCCS	[M-H]-	217.937	30932474
DeepCCS	[M-2H]-	254.48	30932474
DeepCCS	[M+Na]+	230.772	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleoylcarnitine	CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	3623.7	Standard polar	33892256
Oleoylcarnitine	CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2640.9	Standard non polar	33892256
Oleoylcarnitine	CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2954.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oleoylcarnitine,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	2969.3	Semi standard non polar	33892256
Oleoylcarnitine,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	3198.3	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 - Oleoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleoylcarnitine 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 - Oleoylcarnitine 10V, Positive-QTOF	splash10-004i-0000900000-c76c8c1a67e6b24de5c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoylcarnitine 20V, Positive-QTOF	splash10-002r-9000500000-4902a8769b2895518a15	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.040-0.210 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.11 (0.08-0.15) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	0.87 +/- 0.58 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	0.20 +/- 0.28 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	0.17 (0.14-0.26) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.64 +/- 0.49 uM	Children (1-13 years old)	Both	Acetaminophen overdose	24521011	details
Blood	Detected and Quantified	0.107 +/- 0.038 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.111 +/- 0.039 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

601665 (Obesity)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023614

KNApSAcK ID

Not Available

Chemspider ID

21403150

KEGG Compound ID

Not Available

BioCyc ID

CPD-20402

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46907933

PDB ID

Not Available

ChEBI ID

84651

Food Biomarker Ontology

Not Available

VMH ID

ODECRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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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 ]
Cao B, Wang D, Pan Z, McIntyre RS, Brietzke E, Subramanieapillai M, Nozari Y, Wang J: Metabolic profiling for water-soluble metabolites in patients with schizophrenia and healthy controls in a Chinese population: A case-control study. World J Biol Psychiatry. 2020 Jun;21(5):357-367. doi: 10.1080/15622975.2019.1615639. Epub 2019 Jun 4. [PubMed:31161852 ]
Kalim S, Clish CB, Wenger J, Elmariah S, Yeh RW, Deferio JJ, Pierce K, Deik A, Gerszten RE, Thadhani R, Rhee EP: A plasma long-chain acylcarnitine predicts cardiovascular mortality in incident dialysis patients. J Am Heart Assoc. 2013 Dec 5;2(6):e000542. doi: 10.1161/JAHA.113.000542. [PubMed:24308938 ]
Kirby T, Walters DC, Shi X, Turgeon C, Rinaldo P, Arning E, Ashcraft P, Bottiglieri T, DiBacco M, Pearl PL, Roullet JB, Gibson KM: Novel biomarkers and age-related metabolite correlations in plasma and dried blood spots from patients with succinic semialdehyde dehydrogenase deficiency. Orphanet J Rare Dis. 2020 Sep 23;15(1):261. doi: 10.1186/s13023-020-01522-5. [PubMed:32967698 ]
Wright EL, Baker PR: Neonatal Macrosomia is an Interfering Factor for Analytes on the Colorado State Newborn Screen. J Clin Endocrinol Metab. 2020 Mar 1;105(3). pii: 5775549. doi: 10.1210/clinem/dgz183. [PubMed:32126138 ]
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Showing metabocard for Oleoylcarnitine (HMDB0005065)

MOL for HMDB0005065 (Oleoylcarnitine)

3D MOL for HMDB0005065 (Oleoylcarnitine)

3D SDF for HMDB0005065 (Oleoylcarnitine)

3D-SDF for HMDB0005065 (Oleoylcarnitine)

PDB for HMDB0005065 (Oleoylcarnitine)

3D PDB for HMDB0005065 (Oleoylcarnitine)

SMILES for HMDB0005065 (Oleoylcarnitine)

INCHI for HMDB0005065 (Oleoylcarnitine)

Structure for HMDB0005065 (Oleoylcarnitine)

3D Structure for HMDB0005065 (Oleoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra