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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:41 UTC
Update Date2022-03-07 02:52:17 UTC
HMDB IDHMDB0029796
Secondary Accession Numbers
  • HMDB29796
Metabolite Identification
Common Name(Z)-13-Oxo-9-octadecenoic acid
Description(Z)-13-Oxo-9-octadecenoic acid belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review a small amount of articles have been published on (Z)-13-Oxo-9-octadecenoic acid.
Structure
Data?1582753466
Synonyms
ValueSource
(Z)-13-oxo-9-OctadecenoateGenerator
Diethyl 2,4-diacetyl-2-(hydroxymethyl)pentanedioateHMDB
13-Keto-trans-9-octadecenoateGenerator
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9E)-13-oxooctadec-9-enoic acid
Traditional Name(9E)-13-oxooctadec-9-enoic acid
CAS Registry Number38205-11-7
SMILES
CCCCCC(=O)CC\C=C\CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9H,2-6,8,10-16H2,1H3,(H,20,21)/b9-7+
InChI KeyLDYZTLZOFONHNA-VQHVLOKHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP5.87ALOGPS
logP5.6ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity88.04 m³·mol⁻¹ChemAxon
Polarizability37.43 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]+177.61431661259
DarkChem[M-H]-179.9631661259
DeepCCS[M+H]+178.62330932474
DeepCCS[M-H]-176.26530932474
DeepCCS[M-2H]-210.24930932474
DeepCCS[M+Na]+186.31130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Z)-13-Oxo-9-octadecenoic acidCCCCCC(=O)CC\C=C\CCCCCCCC(O)=O3565.3Standard polar33892256
(Z)-13-Oxo-9-octadecenoic acidCCCCCC(=O)CC\C=C\CCCCCCCC(O)=O2208.4Standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acidCCCCCC(=O)CC\C=C\CCCCCCCC(O)=O2281.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(Z)-13-Oxo-9-octadecenoic acid,1TMS,isomer #1CCCCCC(=O)CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C2395.3Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,1TMS,isomer #2CCCCCC(=CC/C=C/CCCCCCCC(=O)O)O[Si](C)(C)C2522.7Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,1TMS,isomer #3CCCCC=C(CC/C=C/CCCCCCCC(=O)O)O[Si](C)(C)C2499.6Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TMS,isomer #1CCCCCC(=CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2510.8Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TMS,isomer #1CCCCCC(=CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2468.3Standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TMS,isomer #2CCCCC=C(CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2472.9Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TMS,isomer #2CCCCC=C(CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2449.0Standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,1TBDMS,isomer #1CCCCCC(=O)CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2641.8Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,1TBDMS,isomer #2CCCCCC(=CC/C=C/CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2754.7Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,1TBDMS,isomer #3CCCCC=C(CC/C=C/CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2720.5Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TBDMS,isomer #1CCCCCC(=CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2992.6Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TBDMS,isomer #1CCCCCC(=CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2813.7Standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TBDMS,isomer #2CCCCC=C(CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2935.6Semi standard non polar33892256
(Z)-13-Oxo-9-octadecenoic acid,2TBDMS,isomer #2CCCCC=C(CC/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2793.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0032-5920000000-65ce3253abe0172f67d92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-014i-9750000000-4d9798db11343b1f9e762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-13-Oxo-9-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-Oxo-9-octadecenoic acid 10V, Positive-QTOFsplash10-002b-0190000000-c3d6a883a92eeb32f4542016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 20V, Positive-QTOFsplash10-0kkj-7980000000-44a19a50da6d2acb00cd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 40V, Positive-QTOFsplash10-0kmu-9720000000-fabc7218dad21620c03c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 10V, Negative-QTOFsplash10-0002-0090000000-a35d937a237a8e4a2b4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 20V, Negative-QTOFsplash10-0002-2390000000-56634537b29ad6228e932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 40V, Negative-QTOFsplash10-0a4l-9410000000-abd3152068d87434b9c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 10V, Negative-QTOFsplash10-0002-0090000000-15a4d16333d2a0a775632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 20V, Negative-QTOFsplash10-002b-2290000000-b6106bd2e599721b4bab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 40V, Negative-QTOFsplash10-0btc-9410000000-e8a41ddcb1b13e17ae972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 10V, Positive-QTOFsplash10-01t9-1390000000-629b51cea92169c6cf442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 20V, Positive-QTOFsplash10-01rb-6950000000-64b5a0bf576feb86671a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-13-Oxo-9-octadecenoic acid 40V, Positive-QTOFsplash10-0a5d-9200000000-46b655282434a7f0aefa2021-09-22Wishart 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 IDFDB001004
KNApSAcK IDNot Available
Chemspider ID30776789
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44612156
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.