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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-23 13:06:02 UTC
Update Date2020-02-26 21:25:43 UTC
HMDB IDHMDB0005065
Secondary Accession Numbers
  • HMDB0062772
  • HMDB05065
  • HMDB62772
Metabolite Identification
Common NameOleoylcarnitine
DescriptionOleoylcarnitine is a long-chain acylcarnitine that accumulates during certain metabolic conditions, such as fasting (PMID: 15653102 ). Oleoylcarnitine has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1582752343
Synonyms
ValueSource
(9Z)-Octadecenoyl-L-carnitineChEBI
(R)-[(9Z)-Octadecenoyl]carnitineChEBI
Acylcarnitine C18:1ChEBI
O-(9Z)-Octadecenoyl-(R)-carnitineChEBI
Oleoyl-L-carnitineChEBI
(Z)-(+-)-3-Carboxy-N,N,N-trimethyl-2-((1-oxo-9-octadecenyl)oxy)-1-propanaminiumHMDB
Oleoylcarnitine, (R-(Z))-isomerHMDB
O-OleoylcarnitineHMDB
(9Z)-Octadec-9-enoylcarnitineHMDB
cis-9-OctadecenoylcarnitineHMDB
(R)-OleoylcarnitineHMDB
OleoylcarnitineChEBI
Chemical FormulaC25H47NO4
Average Molecular Weight425.654
Monoisotopic Molecular Weight425.350508997
IUPAC Name(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry Number38677-66-6
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/b13-12-/t23-/m1/s1
InChI KeyIPOLTUVFXFHAHI-WHIOSMTNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.7e-06 g/LALOGPS
logP2.02ALOGPS
logP2.56ChemAxon
logS-7.9ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity147.4 m³·mol⁻¹ChemAxon
Polarizability53.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.040-0.210 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.11 (0.08-0.15) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified0.87 +/- 0.58 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified0.20 +/- 0.28 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified0.17 (0.14-0.26) uMInfant (0-1 year old)Not Available
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.64 +/- 0.49 uMChildren (1-13 years old)Both
Acetaminophen overdose
details
BloodDetected and Quantified0.107 +/- 0.038 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.111 +/- 0.039 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Obesity
  1. 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
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023614
KNApSAcK IDNot Available
Chemspider ID21403150
KEGG Compound IDNot Available
BioCyc IDCPD-20402
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46907933
PDB IDNot Available
ChEBI ID84651
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot 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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. 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 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.