MiMeDB: Showing metabocard for Oleoylcarnitine (MMDBc0000608)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:01 UTC

Update Date

2024-04-30 19:33:16 UTC

Metabolite ID

MMDBc0000608

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 [Dambrova et al. 2021, Physiological Reviews], 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 at [Dambrova et al. 2021, Physiological Reviews].

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309172007392D          

 30 29  0  0  0  0            999 V2000
   -6.0556   -0.1994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3416   -0.6127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6276   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9136   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1996   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7716   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4808   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6226   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6276    0.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0556    0.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7696    1.0361    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -7.4877    0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7696    1.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6226    1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7634   -0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7634   -1.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0473   -1.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4753   -1.8607    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  1  23   1
M  END


  Mrv1652309172007392D          

 30 29  0  0  0  0            999 V2000
   -6.0556   -0.1994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3416   -0.6127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6276   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9136   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1996   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7716   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4808   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6226   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6276    0.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0556    0.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7696    1.0361    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -7.4877    0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7696    1.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6226    1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7634   -0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7634   -1.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0473   -1.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4753   -1.8607    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  1  23   1
M  END
> <DATABASE_ID>
MMDBc0000608

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C25H48NO4

> <MOLECULAR_WEIGHT>
426.661

> <EXACT_MASS>
426.35778545

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.33187015777146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-carboxy-2-[(9Z)-octadec-9-enoyloxy]propyl]trimethylazanium

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.5607635275282545

> <ALOGPS_LOGS>
-7.32

> <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>
63.6

> <JCHEM_REFRACTIVITY>
136.55820000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-3-carboxy-2-[(9Z)-octadec-9-enoyloxy]propyl]trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0     -11.304  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.971  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.638  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.305  -1.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.973  -0.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.640  -1.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.307  -0.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.974  -1.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.641  -0.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.691  -1.144   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.024  -0.372   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.563  -0.372   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.896  -1.144   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.232  -0.372   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.565  -1.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.898  -0.372   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.231  -1.144   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.563  -0.372   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.896  -1.144   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.229  -0.372   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.638   1.166   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -11.304   1.166   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0     -12.637   1.934   0.000  0.00  0.00           N+1
HETATM   24  C   UNK     0     -13.977   1.163   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.637   3.473   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.229   2.855   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.625  -1.163   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.625  -2.702   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -11.288  -3.473   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -13.954  -3.473   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

Synonyms

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

Molecular Formula

C₂₅H₄₈NO₄

Average Mass

426.661

Monoisotopic Mass

426.35778545

IUPAC Name

[(2R)-3-carboxy-2-[(9Z)-octadec-9-enoyloxy]propyl]trimethylazanium

Traditional Name

[(2R)-3-carboxy-2-[(9Z)-octadec-9-enoyloxy]propyl]trimethylazanium

CAS Registry Number

Not Available

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 fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.2e-05 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.56	ChemAxon
logS	-7.3	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	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	136.56 m³·mol⁻¹	ChemAxon
Polarizability	53.33 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

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000424	L-Carnitine	Oleoylcarnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1988962
MMDBr0000425	Oleoylcarnitine	L-Carnitine	carnitine palmitoyltransferase 2	VMH	1528846 1988962
MMDBr0000426	Oleoylcarnitine	Oleoylcarnitine	solute carrier family 25 (carnitine/acylcarnitine translocase), member 20	VMH	14598172
MMDBr0006762	Oleoylcarnitine	L-Carnitine	Not Available	VMH	30371894
MMDBr0009782	L-Carnitine	Oleoylcarnitine	carnitine palmitoyltransferase 1A (liver)	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Obesity	Decreased	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity	Decreased	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human stool; Human feces; Human mucosa; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.11		0.08	0.15	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	0.17		0.14	0.26	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	0.20	0.28			uM	Children (1-13 years old)	Both	Normal	HMDB	24521011
Human Blood	Detected and Quantified	0.87	0.58			uM	Children (1-13 years old)	Both	Normal	HMDB	24521011
Human Blood	Detected and Quantified	0.107	0.038			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	0.111	0.039			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified			0.040	0.210	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0005065

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023614

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-20402

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46907934

PDB ID

Not Available

ChEBI ID

84651

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Gempel K, von Praun C, Baumkotter J, Lehnert W, Ensenauer R, Gerbitz KD, Bauer MF: "Adult" form of muscular carnitine palmitoyltransferase II deficiency: manifestation in a 2-year-old child. Eur J Pediatr. 2001 Sep;160(9):548-51. doi: 10.1007/s004310100802. [PubMed:11585077 ]
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Iacobazzi V, Pasquali M, Singh R, Matern D, Rinaldo P, Amat di San Filippo C, Palmieri F, Longo N: Response to therapy in carnitine/acylcarnitine translocase (CACT) deficiency due to a novel missense mutation. Am J Med Genet A. 2004 Apr 15;126A(2):150-5. doi: 10.1002/ajmg.a.20573. [PubMed:15057979 ]
Minkler PE, Kerner J, North KN, Hoppel CL: Quantitation of long-chain acylcarnitines by HPLC/fluorescence detection: application to plasma and tissue specimens from patients with carnitine palmitoyltransferase-II deficiency. Clin Chim Acta. 2005 Feb;352(1-2):81-92. doi: 10.1016/j.cccn.2004.02.004. [PubMed:15653102 ]
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Illsinger S, Lucke T, Peter M, Ruiter JP, Wanders RJ, Deschauer M, Handig I, Wuyts W, Das AM: Carnitine-palmitoyltransferase 2 deficiency: novel mutations and relevance of newborn screening. Am J Med Genet A. 2008 Nov 15;146A(22):2925-8. doi: 10.1002/ajmg.a.32545. [PubMed:18925671 ]
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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 ]
Shah SH, Sun JL, Stevens RD, Bain JR, Muehlbauer MJ, Pieper KS, Haynes C, Hauser ER, Kraus WE, Granger CB, Newgard CB, Califf RM, Newby LK: Baseline metabolomic profiles predict cardiovascular events in patients at risk for coronary artery disease. Am Heart J. 2012 May;163(5):844-850.e1. doi: 10.1016/j.ahj.2012.02.005. [PubMed:22607863 ]
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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 ]
Rizza S, Copetti M, Rossi C, Cianfarani MA, Zucchelli M, Luzi A, Pecchioli C, Porzio O, Di Cola G, Urbani A, Pellegrini F, Federici M: Metabolomics signature improves the prediction of cardiovascular events in elderly subjects. Atherosclerosis. 2014 Feb;232(2):260-4. doi: 10.1016/j.atherosclerosis.2013.10.029. Epub 2013 Nov 18. [PubMed:24468136 ]
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Liepinsh E, Makrecka-Kuka M, Volska K, Kuka J, Makarova E, Antone U, Sevostjanovs E, Vilskersts R, Strods A, Tars K, Dambrova M: Long-chain acylcarnitines determine ischaemia/reperfusion-induced damage in heart mitochondria. Biochem J. 2016 May 1;473(9):1191-202. doi: 10.1042/BCJ20160164. Epub 2016 Mar 2. [PubMed:26936967 ]
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Showing metabocard for Oleoylcarnitine (MMDBc0000608)

MOL for #<Metabolite:0x00007f46c801a048>

3D MOL for #<Metabolite:0x00007f46c801a048>

3D SDF for #<Metabolite:0x00007f46c801a048>

3D-SDF for #<Metabolite:0x00007f46c801a048>

PDB for #<Metabolite:0x00007f46c801a048>

3D PDB for #<Metabolite:0x00007f46c801a048>

SMILES for #<Metabolite:0x00007f46c801a048>

INCHI for #<Metabolite:0x00007f46c801a048>

Structure for #<Metabolite:0x00007f46c801a048>

3D Structure for #<Metabolite:0x00007f46c801a048>