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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2020-09-11 01:33:33 UTC
NP-MRD IDNP0000010
Secondary Accession NumbersNone
Natural Product Identification
Common NamePetroselinic acid
DescriptionPetroselinic acid, also known as 18:1N-6 or 6-octadecensaeure, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Petroselinic acid is a weakly acidic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
18:1N-6ChEBI
6-OctadecensaeureChEBI
C18:1N-6ChEBI
Octadec-6-ensaeureChEBI
PetroselinateGenerator
Octadec-6-enoateHMDB
Petroselinic acid, (e)-isomerHMDB
Petroselinic acid, sodium salt, (Z)-isomerHMDB
Petroselenic acidHMDB
Petroselinic acid, (Z)-isomerHMDB
Petroselinic acidMeSH
Chemical FormulaC18H34O2
Average Molecular Weight282.468
Monoisotopic Molecular Weight282.255880335
IUPAC Nameoctadec-6-enoic acid
Traditional Name6-octadecenoic acid
CAS Registry Number593-39-5
SMILES
CCCCCCCCCCCC=CCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)
InChI KeyCNVZJPUDSLNTQU-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Plantae
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.9e-05 g/LALOGPS
logP7.72ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0002080
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012765
KNApSAcK IDNot Available
Chemspider ID11144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPetroselinic acid
METLIN IDNot Available
PubChem Compound11634
PDB IDNot Available
ChEBI ID36022
References
General References
  1. Metzger JO, Bornscheuer U: Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol. 2006 Jun;71(1):13-22. Epub 2006 Apr 8. [PubMed:16604360 ]