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Record Information
Version1.0
Creation Date2016-09-30 22:31:41 UTC
Update Date2020-04-22 15:03:52 UTC
MCDB ID BMDB0000499
Secondary Accession Numbers
  • BMDB00499
  • BMDB0062586
  • BMDB62586
Metabolite Identification
Common Name5-Tetradecenoic acid
Description5-Tetradecenoic acid, also known as (Z)-5-tetradecenoate, 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. 5-Tetradecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Tetradecenoic acid has been linked to the inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency.
Structure
Thumb
Synonyms
ValueSource
5-TetradecenoateGenerator
PhyseterateHMDB
Physeteric acidHMDB
PhysoterateHMDB
Physoteric acidHMDB
(5E)-5-Tetradecenoic acidHMDB
(e)-5-Tetradecenoic acidHMDB
C14:1W9HMDB
FA(14:1(5E))HMDB
FA(14:1n9)HMDB
trans-5-Tetradecenoic acidHMDB
5-Tetradecenoic acidHMDB
Chemical FormulaC14H26O2
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
IUPAC Name(5E)-tetradec-5-enoic acid
Traditional Namephyseteric acid
CAS Registry Number544-66-1
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 KeyAFGUVBVUFZMJMX-MDZDMXLPSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability29.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9500000000-0b0af7482ba8816cc6ab2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g7r-9320000000-cb804ee15a90c6b4b8182017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-7a4f23ca69ff41d25e222017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-5930000000-871f7b73a233ffe1c48f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-b88980b220617e7a49812017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-7f930e0e03b1fa3a9fd42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1390000000-353787f26fcfb5c6dd0b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-53c75124447efe309e952017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-6c6d923a7644bf907b732021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1090000000-f0aa2436f161b1da4f072021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-355a8cd627eeee3a751c2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-9430000000-1fba7cb19884c7c32cd42021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apj-9100000000-bb1fd580717537a9dc0c2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-cb2869d738fb7b21f4a02021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Julliana Isabelle...
details
HMDB IDHMDB0000499
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022089
KNApSAcK IDNot Available
Chemspider ID4445867
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5485
PubChem Compound5282740
PDB IDNot Available
ChEBI ID89393
References
Synthesis ReferenceToyama, 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. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  2. Julliana Isabelle Simionato, Juliana Carla Garcia, Geraldo Tadeu dos Santos, Cláudio Celestino Oliveira, Jesui Vergilio Visentainera and Nilson Evelázio de Souza (2010). Julliana Isabelle Simionato, Juliana Carla Garcia, Geraldo Tadeu dos Santos, Cláudio Celestino Oliveira, Jesui Vergilio Visentainera and Nilson Evelázio de Souza. Validation of the Determination of Fatty Acids in Milk by Gas Chromatography. J. Braz. Chem. Soc., Vol. 21, No. 3, 520-524, 2010.. J. Braz. Chem. Soc..