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Human Metabolome Database Version 3.5

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Showing metabocard for Oleoylcarnitine (HMDB05065)

Record Information
Version 3.5
Creation Date 2006-10-23 07:06:02 -0600
Update Date 2013-02-08 17:13:51 -0700
HMDB ID HMDB05065
Secondary Accession Numbers None
Metabolite Identification
Common Name Oleoylcarnitine
Description Oleoylcarnitine is a long-chain acylcarnitine that accumulates during certain metabolic conditions, such as fasting (PMID: 15653102 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (Z)-(+-)-3-carboxy-N,N,N-trimethyl-2-((1-oxo-9-octadecenyl)oxy)-1-Propanaminium
  2. Acylcarnitine C18:1
  3. Oleoyl-L-carnitine
  4. Oleoylcarnitine
Chemical Formula C25H47NO4
Average Molecular Weight 425.645
Monoisotopic Molecular Weight 425.350508997
IUPAC Name (4S)-4-[(9Z)-octadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name (4S)-4-[(9Z)-octadec-9-enoyloxy]-4-(trimethylaminio)butanoate
CAS Registry Number 38677-66-6
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]([N+](C)(C)C)CCC([O-])=O
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(26(2,3)4)21-22-24(27)28/h12-13,23H,5-11,14-22H2,1-4H3/b13-12-/t23-/m0/s1
InChI Key ASTZXVSQSSBFOS-FRHQNKJESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Carboxylic Acid Salt
  • Dicarboxylic Acid Derivative
  • Quaternary Ammonium Salt
Direct Parent Fatty Acid Esters
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental 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
Predicted Properties
Property Value Source
Water Solubility 6.670E-06 g/L ALOGPS
LogP 1.73 ALOGPS
LogP 2.89 ChemAxon
LogS -7.86 ALOGPS
pKa (strongest acidic) 4.17 ChemAxon
pKa (strongest basic) -7.2 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 66.43 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 147.33 ChemAxon
Polarizability 52.94 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023614
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05065 Link_out
Metagene Link HMDB05065 Link_out
METLIN ID Not Available
PubChem Compound 53477789 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. 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. Pubmed: 15653102 Link_out