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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 08:08:37 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, in tissues from patients with mitochondrial beta-oxidation defects, particularly in very long-chain acyl-CoA dehydrogenase deficiency (VLCADD1/VLCADD2) (PMID 2051892 ), a genetic disorder. 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
ValueSource
(Z)-5-Tetradecenoic acidChEBI
cis-5-Tetradecenoic acidChEBI
(Z)-5-TetradecenoateGenerator
5Z-TetradecenoateGenerator
cis-5-TetradecenoateGenerator
(5Z)- 5-TetradecenoateHMDB
(5Z)- 5-Tetradecenoic acidHMDB
cis-D5-TetradecenoateHMDB
cis-D5-Tetradecenoic acidHMDB
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
DescriptionThis compound 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
Polarizability28.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9500000000-0b0af7482ba8816cc6abView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g7r-9320000000-cb804ee15a90c6b4b818View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-7a4f23ca69ff41d25e22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-5930000000-871f7b73a233ffe1c48fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-b88980b220617e7a4981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-7f930e0e03b1fa3a9fd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1390000000-353787f26fcfb5c6dd0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-53c75124447efe309e95View in MoNA
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
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 ]
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 ]
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
FoodDB 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
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 ]