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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:10:14 UTC
Update Date2021-10-13 08:34:35 UTC
HMDB IDHMDB0041480
Secondary Accession Numbers
  • HMDB41480
Metabolite Identification
Common Name(Z)-13-Octadecenoic acid
Description(Z)-13-Octadecenoic acid is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. (Z)-13-octadecenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, (Z)-13-octadecenoic acid is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. (Z)-13-Octadecenoic acid is a constituent of various lipid fractions from fish and some cooked foods.
Structure
Data?1563863668
Synonyms
ValueSource
(Z)-13-OctadecenoateGenerator
13Z-OctadecenoateHMDB
13-Octadecenoic acidHMDB
13-Octadecenoic acid, (e)-isomerHMDB
13-Octadecenoic acid, sodium salt, (Z)-isomerHMDB
cis-13-Octadecenoic acidHMDB
(13Z)-13-Octadecenoic acidHMDB
(13Z)-OctadecenoateHMDB
(Z)-13-Octadecenoic acidHMDB
Chemical FormulaC18H34O2
Average Molecular Weight282.468
Monoisotopic Molecular Weight282.255880335
IUPAC Name(13Z)-octadec-13-enoic acid
Traditional Name(13Z)-octadec-13-enoic acid
CAS Registry Number13126-39-1
SMILES
CCCC\C=C/CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-6H,2-4,7-17H2,1H3,(H,19,20)/b6-5-
InChI KeyBDLLSHRIFPDGQB-WAYWQWQTSA-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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point26.5 - 27 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP10(7.66) g/LALOGPS
logP10(6.78) g/LChemAxon
logS10(-6.4) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.05531661259
DarkChem[M-H]-177.29331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Z)-13-Octadecenoic acidCCCC\C=C/CCCCCCCCCCCC(O)=O3143.4Standard polar33892256
(Z)-13-Octadecenoic acidCCCC\C=C/CCCCCCCCCCCC(O)=O2094.3Standard non polar33892256
(Z)-13-Octadecenoic acidCCCC\C=C/CCCCCCCCCCCC(O)=O2154.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(Z)-13-Octadecenoic acid,1TMS,isomer #1CCCC/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C2225.8Semi standard non polar33892256
(Z)-13-Octadecenoic acid,1TBDMS,isomer #1CCCC/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2486.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Octadecenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9630000000-4edbe8b90b6f30fc1b8c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Octadecenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9541000000-18a88bfb1c9dd5dad3862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Octadecenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Octadecenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 10V, Positive-QTOFsplash10-014i-0090000000-c07df8fac69478dc192d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 20V, Positive-QTOFsplash10-014r-4590000000-1e96b39182f3370a109b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 40V, Positive-QTOFsplash10-0076-8930000000-3da2ada827252be2fde62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 10V, Negative-QTOFsplash10-001i-0090000000-1b80c5a75129c09b94ae2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 20V, Negative-QTOFsplash10-01qi-0090000000-594a087f3d32d156a36b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 40V, Negative-QTOFsplash10-0a4l-9130000000-78479e11a103c868854a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 10V, Negative-QTOFsplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 20V, Negative-QTOFsplash10-01q9-1090000000-676fc61b5e3d5d0e58592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 40V, Negative-QTOFsplash10-0006-9220000000-87d90b2e18cee3f024b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 10V, Positive-QTOFsplash10-00lr-4190000000-66467fcf35ab48987e8f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 20V, Positive-QTOFsplash10-05nb-9410000000-0487cdfe93d429e74a772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Octadecenoic acid 40V, Positive-QTOFsplash10-0aor-9000000000-c1fb70834681e994cbd02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4471866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312441
PDB IDNot Available
ChEBI ID82617
Food Biomarker OntologyNot Available
VMH IDM00019
MarkerDB IDNot Available
Good Scents IDrw1892811
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.