13-Docosenoic acid, (Z)- (CHEM009431)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:04:51 UTC
Update Date2016-11-09 01:13:59 UTC
Accession NumberCHEM009431
Identification
Common Name13-Docosenoic acid, (Z)-
ClassSmall Molecule
DescriptionA docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13Z)-13-Docosenoic acidChEBI
(13Z)-Docosenoic acidChEBI
(Z)-13-Docosenoic acidChEBI
(Z)-Docos-13-enoic acidChEBI
13-cis-Docosenoic acidChEBI
22:1Omega9ChEBI
C22:1N-9ChEBI
cis-13-Docosenoic acidChEBI
cis-Delta(13)-Docosenoic acidChEBI
cis-Eruic acidChEBI
Docos-13C-enoic acidChEBI
ErucasaeureChEBI
(13Z)-13-DocosenoateGenerator
(13Z)-DocosenoateGenerator
(Z)-13-DocosenoateGenerator
(Z)-Docos-13-enoateGenerator
13-cis-DocosenoateGenerator
cis-13-DocosenoateGenerator
cis-delta(13)-DocosenoateGenerator
cis-Δ(13)-docosenoateGenerator
cis-Δ(13)-docosenoic acidGenerator
cis-EruateGenerator
Docos-13C-enoateGenerator
ErucateGenerator
13-Docosenoic acidHMDB
Erucic acid, (Z)-isomerHMDB
13-DocosenoateHMDB
13-Docosenoic acid (acd/name 4.0)HMDB
cis-Erucic acidHMDB
delta 13-cis-DocosenoateHMDB
delta 13-cis-Docosenoic acidHMDB
Delta.13-cis-docosenoateHMDB
Delta.13-cis-docosenoic acidHMDB
Prifrac 2990HMDB
(Z)-Erucic acidHMDB
13(Z)-Docosenoic acidHMDB
FA(22:1(13Z))HMDB
FA(22:1n9)HMDB
cis-13-Erucic acidHMDB
delta13-cis-Docosenoic acidHMDB
Δ13-cis-docosenoic acidHMDB
Erucic acidHMDB
Chemical FormulaC22H42O2
Average Molecular Mass338.568 g/mol
Monoisotopic Mass338.318 g/mol
CAS Registry Number112-86-7
IUPAC Name(13Z)-docos-13-enoic acid
Traditional Nameerucic acid
SMILESCCCCCCCC\C=C/CCCCCCCCCCCC(O)=O
InChI IdentifierInChI=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/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
InChI KeyDPUOLQHDNGRHBS-KTKRTIGZSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP8.97ALOGPS
logP8.56ChemAxon
logS-7.2ALOGPS
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
Polarizability45.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-6900000000-5e6160a7a5341d6f55deSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-6900000000-5e6160a7a5341d6f55deSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9670000000-abb8d10b97d3c63c8480Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fmv-9452000000-be430773e3b82d00352dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0009000000-c637d7d9283da6dae58cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05ur-9100000000-4dfe9f552da0b8ea6e7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0159-9000000000-867fce64ced7de3a289eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-014i-0009000000-a67df2342edb038f0647Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0019000000-0026b53b7b328f5e5154Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00dr-1119000000-fa6979100366edcb2892Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0fki-5829000000-ff16fd0e5a988fe38fa4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0apj-9200000000-27116cd4b609b88b4005Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0api-9100000000-0f82260b5b86e3b06b2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-0aor-9000000000-0a3061b18adfe4ddad07Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00di-0129000000-fa49cfc1738521b925d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-000i-0290000000-b4f9a52c100defbf8a39Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-014i-0090000000-02a20bc6ce898cb3824cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-07l5-0950000000-0ca01024ab3b5ad027ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0udi-0319000000-7b31f345d0546a6c25abSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00di-2209000000-d03f3b30c822ce8c5e26Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00di-9608000000-2fc5f27c0bd54f0c003aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059t-9502000000-8f68c9dbb8e1467805f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-05nb-9300000000-0701894bd7e9b3d37f40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-c06b5c8f2b9044af1c34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g3-5695000000-55896e489497235f6a67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9880000000-69f41c34dca989e6c810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-cfb3c7afc93ecf28f3daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-1039000000-c2dd9360fea23806c313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9131000000-393859815e6c1359d6dfSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a5c-9300000000-53ce9b6b1bd7db601866Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002068
FooDB IDFDB004287
Phenol Explorer IDNot Available
KNApSAcK IDC00001217
BiGG IDNot Available
BioCyc IDCPD-14292
METLIN ID6470
PDB IDNot Available
Wikipedia LinkErucic_acid
Chemspider ID4444561
ChEBI ID28792
PubChem Compound ID5281116
Kegg Compound IDC08316
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1170010
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=7847331
3. Rizzo WB, Leshner RT, Odone A, Dammann AL, Craft DA, Jensen ME, Jennings SS, Davis S, Jaitly R, Sgro JA: Dietary erucic acid therapy for X-linked adrenoleukodystrophy. Neurology. 1989 Nov;39(11):1415-22.
4. Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21.
5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.