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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:17 UTC
Update Date2020-02-26 21:24:18 UTC
HMDB IDHMDB0002884
Secondary Accession Numbers
  • HMDB02884
Metabolite Identification
Common NameCetoleic acid
DescriptionCetoleic acid, also known as 22:1, N-11 cis or cetoleate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Based on a literature review a significant number of articles have been published on Cetoleic acid.
Structure
Data?1582752258
Synonyms
ValueSource
(Z)-11-Docosenoic acidChEBI
(Z)-Docos-11-enoic acidChEBI
22:1, N-11 cisChEBI
C22:1, N-11 cisChEBI
CetoleinsaeureChEBI
cis-11-Docosenoic acidChEBI
cis-Delta(11)-Docosenoic acidChEBI
cis-Docos-11-enoic acidChEBI
Docos-11C-enoic acidChEBI
Docos-11C-ensaeureChEBI
(Z)-11-DocosenoateGenerator
(Z)-Docos-11-enoateGenerator
cis-11-DocosenoateGenerator
cis-delta(11)-DocosenoateGenerator
cis-Δ(11)-docosenoateGenerator
cis-Δ(11)-docosenoic acidGenerator
cis-Docos-11-enoateGenerator
Docos-11C-enoateGenerator
CetoleateGenerator
(11Z)-Docos-11-enoateHMDB
(11Z)-Docos-11-enoic acidHMDB
11Z-DocosenoateHMDB
11Z-Docosenoic acidHMDB
cis-CetoleateHMDB
cis-Cetoleic acidHMDB
Cetoleic acid, (Z)-isomerHMDB
11-Docosenoic acidHMDB
Cetoleic acid, (e)-isomerHMDB
(11Z)-11-Docosenoic acidHMDB
FA(22:1(11Z))HMDB
FA(22:1n11)HMDB
Cetoleic acidMeSH
Chemical FormulaC22H42O2
Average Molecular Weight338.5677
Monoisotopic Molecular Weight338.318480588
IUPAC Name(11Z)-docos-11-enoic acid
Traditional Namecetoleic acid
CAS Registry Number1002-96-6
SMILES
CCCCCCCCCC\C=C/CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h11-12H,2-10,13-21H2,1H3,(H,23,24)/b12-11-
InChI KeyKJDZDTDNIULJBE-QXMHVHEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP10(8.97) g/LALOGPS
logP10(8.56) g/LChemAxon
logS10(-7.2) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity105.81 m³·mol⁻¹ChemAxon
Polarizability45.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.41631661259
DarkChem[M-H]-193.43831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cetoleic acid,1TMS,#1CCCCCCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C2619.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cetoleic acid,1TBDMS,#1CCCCCCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2902.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cetoleic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8690000000-81ccb0034d9fbf5f12242017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cetoleic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00c0-9561000000-5be3f8bb2000a8e333682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cetoleic 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 - Cetoleic acid 10V, Positive-QTOFsplash10-00di-0019000000-c22a658b75d35ea6e29b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 20V, Positive-QTOFsplash10-0ffx-5795000000-bd1aa50ad9a8a48c6ed42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 40V, Positive-QTOFsplash10-004l-8980000000-b3b28a820db2bdd2e0412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 10V, Negative-QTOFsplash10-000i-0019000000-cfb3c7afc93ecf28f3da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 20V, Negative-QTOFsplash10-00ku-1039000000-c2dd9360fea23806c3132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 40V, Negative-QTOFsplash10-052f-9131000000-fbc3abdbc2044cc6b9a32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 10V, Negative-QTOFsplash10-000i-0009000000-c73eab4fa862703f84a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 20V, Negative-QTOFsplash10-00kr-1009000000-7dabb6682d31f35b3fc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 40V, Negative-QTOFsplash10-0006-9021000000-db7287c4480b80bde6092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 10V, Positive-QTOFsplash10-0079-2109000000-ae3d9e03c37915fd05d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 20V, Positive-QTOFsplash10-05g0-9348000000-e7004c953c82e5e8ee102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetoleic acid 40V, Positive-QTOFsplash10-0a4i-9100000000-e971ca24b71f677c65462021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0295 +/- 0.384 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003004
KNApSAcK IDNot Available
Chemspider ID4445898
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID261
PubChem Compound5282771
PDB IDNot Available
ChEBI ID32428
Food Biomarker OntologyNot Available
VMH IDM01582
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Loew FM, Schiefer B, Laxdal VA, Prasad K, Forsyth GW, Ackman RG, Olfert ED, Bell JM: Effects of plant and animal lipids rich in docosenoic acids on the myocardium of Cynomolgus monkeys. Nutr Metab. 1978;22(4):201-17. [PubMed:416402 ]
  2. Hagfors L, Nilsson I, Skoldstam L, Johansson G: Fat intake and composition of fatty acids in serum phospholipids in a randomized, controlled, Mediterranean dietary intervention study on patients with rheumatoid arthritis. Nutr Metab (Lond). 2005 Oct 10;2:26. [PubMed:16216119 ]
  3. Schiefer B, Loew FM, Laxdal V, Prasad K, Forsyth G, Ackman RG, Olfert ED: Morphologic effects of dietary plant and animal lipids rich in docosenoic acids on heart and skeletal muscle of cynomolgus monkeys. Am J Pathol. 1978 Mar;90(3):551-64. [PubMed:415615 ]