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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Tetradecenoic acid (HMDB00499)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:42 -0700
HMDB ID HMDB00499
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Tetradecenoic acid
Description 5-Tetradecenoic acid is an intermediate of unsaturated fatty acid metabolism found in plasma of patients with very-long-chain acyl-CoA dehydrogenase (VLCAD) deficiency (PMID 7586519 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5-Tetradecenoate
  2. 5-Tetradecenoic acid
  3. Physeterate
  4. Physeteric acid
  5. Physoterate
  6. Physoteric acid
Chemical Formula C14H26O2
Average Molecular Weight 226.355
Monoisotopic Molecular Weight 226.193280076
IUPAC Name (5E)-tetradec-5-enoic acid
Traditional IUPAC Name physeteric acid
CAS Registry Number 544-66-1
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 Key AFGUVBVUFZMJMX-MDZDMXLPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Unsaturated Fatty Acids
Ontology
Status Detected and 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
  • Cytoplasm
  • 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 0.0018 g/L ALOGPS
LogP 5.77 ALOGPS
LogP 5.01 ChemAxon
LogS -5.10 ALOGPS
pKa (strongest acidic) 4.89 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 69 ChemAxon
Polarizability 29.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.5 (0.6 - 2.3) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
50.0 (14.3 - 84.0) uM Adult (>18 years old) Not Specified Very Long Chain Acyl-CoA Dehydrogenase Deficiency Not Available
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  • 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 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022078
    KNApSAcK ID Not Available
    Chemspider ID 4445867 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB00499 Link_out
    Metagene Link HMDB00499 Link_out
    METLIN ID 5485 Link_out
    PubChem Compound 5282740 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Toyama, 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 Link_out
    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 Link_out