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

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
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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Showing metabocard for Oleoylcarnitine (MMDBc0000608)

MOL for #<Metabolite:0x00007fb7abd7b0a8>

3D MOL for #<Metabolite:0x00007fb7abd7b0a8>

3D SDF for #<Metabolite:0x00007fb7abd7b0a8>

3D-SDF for #<Metabolite:0x00007fb7abd7b0a8>

PDB for #<Metabolite:0x00007fb7abd7b0a8>

3D PDB for #<Metabolite:0x00007fb7abd7b0a8>

SMILES for #<Metabolite:0x00007fb7abd7b0a8>

INCHI for #<Metabolite:0x00007fb7abd7b0a8>

Structure for #<Metabolite:0x00007fb7abd7b0a8>

3D Structure for #<Metabolite:0x00007fb7abd7b0a8>