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Human Metabolome Database Version 3.5

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Showing metabocard for 5Z-Tetradecenoic acid (HMDB00521)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:27:18 -0600
HMDB ID HMDB00521
Secondary Accession Numbers
  • HMDB00499
Metabolite Identification
Common Name 5Z-Tetradecenoic acid
Description 5Z-Tetradecenoic acid is an intermediate of unsaturated fatty acid oxidation that is incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects, particularly in very long-chain acyl-CoA dehydrogenase deficiency (VLCADD1/ VLCADD2). (PMID 2051892 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (5Z)- 5-Tetradecenoate
  2. (5Z)- 5-Tetradecenoic acid
  3. (Z)-5-Tetradecenoate
  4. (Z)-5-Tetradecenoic acid
  5. 5Z-Tetradecenoate
  6. 5Z-Tetradecenoic acid
  7. cis-5-Tetradecenoate
  8. cis-5-Tetradecenoic acid
  9. cis-D5-Tetradecenoate
  10. cis-D5-Tetradecenoic acid
Chemical Formula C14H26O2
Average Molecular Weight 226.355
Monoisotopic Molecular Weight 226.193280076
IUPAC Name (5Z)-tetradec-5-enoic acid
Traditional IUPAC Name (5Z)-tetradec-5-enoic acid
CAS Registry Number 5684-70-8
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-KTKRTIGZSA-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 (predicted from logP)
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 28.74 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.5 (0.6 - 2.3) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 215 +/- 174 uM Children (1-13 year old) Both Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Blood Detected and Quantified 111 +/- 94 uM Children (1-13 year old) Both Long-chain 3-hydroxyacyl-CoA dehydrogenase
Blood Detected and Quantified 68 +/- 85 uM Children (1-13 year old) Both Multiple acyl-CoA dehydrogenase deficiency
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  • Divry P, Vianey-Saban C, Mathieu M: Determination of total fatty acids in plasma: cis-5-tetradecenoic acid (C14:1 omega-9) in the diagnosis of long-chain fatty acid oxidation defects. J Inherit Metab Dis. 1999 May;22(3):286-8. Pubmed: 10384388 Link_out
    Long-chain-3-hydroxyacyl CoA dehydrogenase deficiency
    • Divry P, Vianey-Saban C, Mathieu M: Determination of total fatty acids in plasma: cis-5-tetradecenoic acid (C14:1 omega-9) in the diagnosis of long-chain fatty acid oxidation defects. J Inherit Metab Dis. 1999 May;22(3):286-8. Pubmed: 10384388 Link_out
      Multiple acyl-CoA dehydrogenase deficiency
      • Divry P, Vianey-Saban C, Mathieu M: Determination of total fatty acids in plasma: cis-5-tetradecenoic acid (C14:1 omega-9) in the diagnosis of long-chain fatty acid oxidation defects. J Inherit Metab Dis. 1999 May;22(3):286-8. Pubmed: 10384388 Link_out
        Associated OMIM IDs
        • 231680 Link_out (Multiple acyl-CoA dehydrogenase deficiency)
        DrugBank ID Not Available
        DrugBank Metabolite ID Not Available
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB022089
        KNApSAcK ID Not Available
        Chemspider ID 4471825 Link_out
        KEGG Compound ID Not Available
        BioCyc ID Not Available
        BiGG ID Not Available
        Wikipedia Link Not Available
        NuGOwiki Link HMDB00521 Link_out
        Metagene Link HMDB00521 Link_out
        METLIN ID 5506 Link_out
        PubChem Compound 5312400 Link_out
        PDB ID Not Available
        ChEBI ID Not Available
        References
        Synthesis Reference Jin, Shiow Jen; Tserng, Kou Yi. Metabolic origins of urinary unsaturated dicarboxylic acids. Biochemistry (1990), 29(37), 8540-7.
        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. Holdsworth JE, Ratledge C: Triacylglycerol synthesis in the oleaginous yeast Candida curvata D. Lipids. 1991 Feb;26(2):111-8. Pubmed: 2051892 Link_out