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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:14 UTC
HMDB IDHMDB0000499
Secondary Accession Numbers
  • HMDB00499
Metabolite Identification
Common Name5-Tetradecenoic acid
Description5-Tetradecenoic acid (CAS: 544-66-1), also known as physeterate or physeteric acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 5-tetradecenoic acid is considered to be a fatty acid lipid molecule. 5-Tetradecenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 5-Tetradecenoic acid can be found primarily in blood. Within the cell, 5-tetradecenoic acid is primarily located in the cytoplasm and in the membrane. It can also be found in the extracellular space. 5-Tetradecenoic acid is an intermediate of unsaturated fatty acid metabolism found in the plasma of patients with very long chain acyl-CoA dehydrogenase (VLCAD) deficiency, a genetic disorder (PMID: 7586519 ).
Structure
Data?1563860654
Synonyms
ValueSource
5-TetradecenoateGenerator
PhyseterateHMDB
Physeteric acidHMDB
PhysoterateHMDB
Physoteric acidHMDB
(5E)-5-Tetradecenoic acidHMDB
(e)-5-Tetradecenoic acidHMDB
C14:1W9HMDB
FA(14:1(5E))HMDB
FA(14:1n9)HMDB
trans-5-Tetradecenoic acidHMDB
5-Tetradecenoic acidHMDB
Chemical FormulaC14H26O2
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
IUPAC Name(5E)-tetradec-5-enoic acid
Traditional Namephyseteric acid
CAS Registry Number5684-69-5
SMILES
CCCCCCCC\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+
InChI KeyAFGUVBVUFZMJMX-MDZDMXLPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

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 Solubility0.0018 g/LALOGPS
logP5.77ALOGPS
logP5.01ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability29.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9500000000-0b0af7482ba8816cc6abJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g7r-9320000000-cb804ee15a90c6b4b818JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-7a4f23ca69ff41d25e22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-5930000000-871f7b73a233ffe1c48fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-b88980b220617e7a4981JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-7f930e0e03b1fa3a9fd4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1390000000-353787f26fcfb5c6dd0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-53c75124447efe309e95JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.5 (0.6 - 2.3) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified50.0 (14.3 - 84.0) uMAdult (>18 years old)Not SpecifiedVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]
Associated OMIM IDs
  • 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022089
KNApSAcK IDNot Available
Chemspider ID4445867
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5485
PubChem Compound5282740
PDB IDNot Available
ChEBI ID89393
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceToyama, Yoshiyuki; Tsuchiya, Tomotaro. The separation of physeteric acid from sardine and pilot-whale oils. Kogyo Kagaku Zasshi (1935), 38 Suppl. binding 680-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
  2. Onkenhout W, Venizelos V, Scholte HR, De Klerk JB, Poorthuis BJ: Intermediates of unsaturated fatty acid oxidation are incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects. J Inherit Metab Dis. 2001 Jun;24(3):337-44. [PubMed:11486898 ]
  3. Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]