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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000521
Secondary Accession Numbers
  • HMDB00521
Metabolite Identification
Common Name5Z-Tetradecenoic acid
Description5Z-Tetradecenoic acid is an intermediate of unsaturated fatty acid oxidation that is incorporated in triglycerides, but not in phospholipids. 5Z-Tetradecenoic acid is found in the tissues of patients with mitochondrial beta-oxidation defects, particularly in very long-chain acyl-CoA dehydrogenase deficiency (VLCADD1/VLCADD2), a genetic disorder (PMID: 2051892 ). 5Z-Tetradecenoic acid is also found to be associated with long-chain 3-hydroxyacyl-CoA dehydrogenase and multiple acyl-CoA dehydrogenase deficiency (MADD), which are also inborn errors of metabolism.
Structure
Thumb
Synonyms
Chemical FormulaC14H26O2
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
IUPAC Name(5Z)-tetradec-5-enoic acid
Traditional Namecis-5-tetradecenoic acid
CAS Registry Number5684-70-8
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 KeyAFGUVBVUFZMJMX-KTKRTIGZSA-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 effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.94 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.5 (0.6 - 2.3) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<2 uMChildren (1 - 13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified215 +/- 174 uMChildren (1-13 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
BloodDetected and Quantified111 +/- 94 uMChildren (1-13 years old)BothLong-chain 3-hydroxyacyl-CoA dehydrogenase deficiency details
BloodDetected and Quantified68 +/- 85 uMChildren (1-13 years old)BothMultiple acyl-CoA dehydrogenase deficiency details
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. 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 ]
Long-chain-3-hydroxyacyl CoA dehydrogenase deficiency
  1. 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 ]
Multiple acyl-CoA dehydrogenase deficiency
  1. 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 ]
Associated OMIM IDs
  • 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
  • 231680 (Multiple acyl-CoA dehydrogenase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022089
KNApSAcK IDNot Available
Chemspider ID4471825
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5506
PubChem Compound5312400
PDB IDNot Available
ChEBI ID70716
Food Biomarker OntologyNot Available
VMH IDM02745
MarkerDB IDMDB00000181
Good Scents IDrw1076811
References
Synthesis ReferenceJin, 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 ]
  2. Holdsworth JE, Ratledge C: Triacylglycerol synthesis in the oleaginous yeast Candida curvata D. Lipids. 1991 Feb;26(2):111-8. [PubMed:2051892 ]