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Showing NP-Card for Erucic acid (NP0000021)

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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2020-09-11 01:14:53 UTC
NP-MRD IDNP0000021
Secondary Accession NumbersNone
Natural Product Identification
Common NameErucic acid
DescriptionErucic acid, also known as cis-eruic acid or 22:1Omega9, 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. Erucic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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 Weight338.5677
Monoisotopic Molecular Weight338.318480588
IUPAC Name(13Z)-docos-13-enoic acid
Traditional Nameerucic acid
CAS Registry Number112-86-7
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCC(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/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
InChI KeyDPUOLQHDNGRHBS-KTKRTIGZSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesPlantae
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point33.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0002068
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004287
KNApSAcK IDC00001217
Chemspider ID4444561
KEGG Compound IDC08316
BioCyc IDCPD-14292
BiGG IDNot Available
Wikipedia LinkErucic_acid
METLIN ID6470
PubChem Compound5281116
PDB IDNot Available
ChEBI ID28792
References
General References
  1. 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. [PubMed:2682348 ]
  2. 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. [PubMed:16581239 ]