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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
Data?1582752136
Synonyms
ValueSource
(Z)-5-Tetradecenoic acidChEBI
cis-5-Tetradecenoic acidChEBI
(Z)-5-TetradecenoateGenerator
cis-5-TetradecenoateGenerator
5Z-TetradecenoateGenerator
5-TetradecenoateHMDB
(5Z)- 5-TetradecenoateHMDB
(5Z)- 5-Tetradecenoic acidHMDB
cis-D5-TetradecenoateHMDB
cis-D5-Tetradecenoic acidHMDB
PhyseterateHMDB
(5Z)-5-Tetradecenoic acidHMDB
C14:1W9HMDB
FA(14:1(5Z))HMDB
FA(14:1n9)HMDB
Physeteric acidHMDB
Physoteric acidHMDB
cis-Tetradec-5-enoateHMDB
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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.98731661259
DarkChem[M-H]-159.87331661259
AllCCS[M+H]+160.70432859911
AllCCS[M-H]-163.08932859911
DeepCCS[M+H]+161.86930932474
DeepCCS[M-H]-157.84830932474
DeepCCS[M-2H]-195.37930932474
DeepCCS[M+Na]+171.05730932474
AllCCS[M+H]+160.732859911
AllCCS[M+H-H2O]+157.332859911
AllCCS[M+NH4]+163.932859911
AllCCS[M+Na]+164.832859911
AllCCS[M-H]-163.132859911
AllCCS[M+Na-2H]-164.432859911
AllCCS[M+HCOO]-165.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5Z-Tetradecenoic acidCCCCCCCC\C=C/CCCC(O)=O2690.8Standard polar33892256
5Z-Tetradecenoic acidCCCCCCCC\C=C/CCCC(O)=O1704.8Standard non polar33892256
5Z-Tetradecenoic acidCCCCCCCC\C=C/CCCC(O)=O1758.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5Z-Tetradecenoic acid,1TMS,isomer #1CCCCCCCC/C=C\CCCC(=O)O[Si](C)(C)C1827.8Semi standard non polar33892256
5Z-Tetradecenoic acid,1TBDMS,isomer #1CCCCCCCC/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2062.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Tetradecenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9500000000-0b0af7482ba8816cc6ab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Tetradecenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0g7r-9320000000-cb804ee15a90c6b4b8182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Tetradecenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5Z-Tetradecenoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 10V, Positive-QTOFsplash10-0a4i-0290000000-7a4f23ca69ff41d25e222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 20V, Positive-QTOFsplash10-0a7i-5930000000-871f7b73a233ffe1c48f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 40V, Positive-QTOFsplash10-052f-9500000000-b88980b220617e7a49812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 10V, Negative-QTOFsplash10-004i-0190000000-7f930e0e03b1fa3a9fd42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 20V, Negative-QTOFsplash10-057i-1390000000-353787f26fcfb5c6dd0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 40V, Negative-QTOFsplash10-0a4l-9400000000-53c75124447efe309e952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 10V, Positive-QTOFsplash10-0a7i-9430000000-1fba7cb19884c7c32cd42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 20V, Positive-QTOFsplash10-0apj-9100000000-bb1fd580717537a9dc0c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 40V, Positive-QTOFsplash10-05mo-9000000000-cb2869d738fb7b21f4a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 10V, Negative-QTOFsplash10-004i-0090000000-6c6d923a7644bf907b732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 20V, Negative-QTOFsplash10-056r-1090000000-f0aa2436f161b1da4f072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5Z-Tetradecenoic acid 40V, Negative-QTOFsplash10-052f-9400000000-355a8cd627eeee3a751c2021-09-22Wishart LabView Spectrum
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 ]