Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:57 UTC
Update Date2022-03-07 02:52:23 UTC
HMDB IDHMDB0029978
Secondary Accession Numbers
  • HMDB29978
Metabolite Identification
Common NameAvenoleic acid
DescriptionAvenoleic acid, also known as avenoleate, 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 Avenoleic acid.
Structure
Data?1563861919
Synonyms
ValueSource
AvenoleateGenerator
15-Hydroxylinoleic acidHMDB
15R-Hydroxylinoleic acidHMDB
15-Hydroxy-9Z,12Z-octadecadienoateGenerator
Chemical FormulaC18H32O3
Average Molecular Weight296.4449
Monoisotopic Molecular Weight296.23514489
IUPAC Name(9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid
Traditional Name(9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid
CAS Registry Number177931-23-6
SMILES
CCCC(O)C\C=C/C\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O3/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18(20)21/h4,6,10,12,17,19H,2-3,5,7-9,11,13-16H2,1H3,(H,20,21)/b6-4-,12-10-
InChI KeyMZQXAWAWDWCIKG-OHPMOLHNSA-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
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.0032 g/LALOGPS
logP5.77ALOGPS
logP5.04ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.19 m³·mol⁻¹ChemAxon
Polarizability35.98 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]+178.11131661259
DarkChem[M-H]-181.58531661259
DeepCCS[M+H]+178.11530932474
DeepCCS[M-H]-175.75730932474
DeepCCS[M-2H]-208.68430932474
DeepCCS[M+Na]+184.20830932474
AllCCS[M+H]+181.132859911
AllCCS[M+H-H2O]+178.132859911
AllCCS[M+NH4]+183.832859911
AllCCS[M+Na]+184.632859911
AllCCS[M-H]-180.332859911
AllCCS[M+Na-2H]-181.932859911
AllCCS[M+HCOO]-183.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Avenoleic acidCCCC(O)C\C=C/C\C=C/CCCCCCCC(O)=O3593.4Standard polar33892256
Avenoleic acidCCCC(O)C\C=C/C\C=C/CCCCCCCC(O)=O2106.9Standard non polar33892256
Avenoleic acidCCCC(O)C\C=C/C\C=C/CCCCCCCC(O)=O2327.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Avenoleic acid,1TMS,isomer #1CCCC(C/C=C\C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C2451.9Semi standard non polar33892256
Avenoleic acid,1TMS,isomer #2CCCC(O)C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2374.5Semi standard non polar33892256
Avenoleic acid,2TMS,isomer #1CCCC(C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2441.1Semi standard non polar33892256
Avenoleic acid,1TBDMS,isomer #1CCCC(C/C=C\C/C=C\CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2695.0Semi standard non polar33892256
Avenoleic acid,1TBDMS,isomer #2CCCC(O)C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2620.9Semi standard non polar33892256
Avenoleic acid,2TBDMS,isomer #1CCCC(C/C=C\C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2901.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Avenoleic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9550000000-f455ca712bdbdf77df472017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Avenoleic acid GC-MS (2 TMS) - 70eV, Positivesplash10-009j-9343200000-7983ff5dc92c1f26c2322017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Avenoleic 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 - Avenoleic acid 10V, Positive-QTOFsplash10-004j-0090000000-2a00dfa9d8161903cedb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 20V, Positive-QTOFsplash10-0h0r-3290000000-c4d933c79561fa9147b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 40V, Positive-QTOFsplash10-0006-9820000000-7220f2131382c20e9d8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 10V, Negative-QTOFsplash10-0002-0090000000-633a0ae31221f0c91d992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 20V, Negative-QTOFsplash10-002b-1090000000-efb8300bf674ab9c87032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 40V, Negative-QTOFsplash10-0a4l-9120000000-8fbd101232c9a1dfa34c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 10V, Negative-QTOFsplash10-0002-0090000000-fed567ebc5f208b44f8b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 20V, Negative-QTOFsplash10-004j-0090000000-df354694d26c43656ede2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 40V, Negative-QTOFsplash10-0596-9330000000-8a66a721654b7b1d66962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 10V, Positive-QTOFsplash10-004j-2390000000-fd2771c6b1c84372913d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 20V, Positive-QTOFsplash10-020r-6950000000-cc197402ead0739114ae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Avenoleic acid 40V, Positive-QTOFsplash10-0apm-9200000000-2d1a36913f45bf7c757b2021-09-24Wishart 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 IDFDB001265
KNApSAcK IDC00000445
Chemspider ID29814126
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75536015
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.