Showing Compound Card for Heptanoic acid (CDB000381)

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Record Information
Version1.0
Created at2020-03-19 00:34:04 UTC
Updated at2020-11-18 16:35:08 UTC
CannabisDB IDCDB000381
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHeptanoic acid
DescriptionHeptanoic acid or heptanoate, also known as enanthylic acid, or enanthic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid. It belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Heptanoate is a very weakly acidic compound, is slightly soluble in water, but very soluble in ethanol and ether. It is an oily liquid with an unpleasant, rancid odor that contributes to the odor of some rancid oils. Present in essential oils, such as violet leaf oil, palm oil, it is also found in apple, feijoa fruit, clove bud, ginger, black tea, morello cherry, grapes, rice bran, scallops, leek and other foodstuffs such as strawberry jam, soups and sauces. Heptanoic acid is one of several saturated fatty acids isolated from the oil of cannabis seeds (PMID: 6991645 ). Heptanoic acid is used in the preparation of esters, such as ethyl heptanoate, which are used in fragrances and as artificial flavors. It is one of many additives in cigarettes. Heptanoic acid is used to esterify steroids in the preparation of drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate, and methenolone enanthate (Primobolan). It is used as one of the components in washing solutions and used to assist lye peeling (by immersion into a lye solution) of fruit and vegetables.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(7:0)ChEBI
1-HexanecarboxylateChEBI
CH3-[CH2]5-COO(-)ChEBI
EnanthateChEBI
EnanthylateChEBI
Heptanoic acid, ion(1-)ChEBI
HeptoateChEBI
HeptylateChEBI
N-HeptanoateChEBI
N-HeptoateChEBI
N-HeptylateChEBI
OenanthateChEBI
OenanthylateChEBI
1-Hexanecarboxylic acidGenerator
Enanthic acidGenerator
Enanthylic acidGenerator
Heptanoate, ion(1-)Generator
Heptoic acidGenerator
Heptylic acidGenerator
N-Heptanoic acidGenerator
N-Heptoic acidGenerator
N-Heptylic acidGenerator
Oenanthic acidGenerator
Oenanthylic acidGenerator
Heptanoic acidGenerator
Chemical FormulaC7H13O2
Average Molecular Weight129.18
Monoisotopic Molecular Weight129.0921
IUPAC Nameheptanoate
Traditional Nameenanthate
CAS Registry Number7563-37-3
SMILES
CCCCCCC([O-])=O
InChI Identifier
InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)/p-1
InChI KeyMNWFXJYAOYHMED-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain 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
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point−7.5 °CWikipedia
Boiling Point223 °CWikipedia
Water Solubility0.24 g/100 mL at 15 °CWikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.45ALOGPS
logP2.26ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)5.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.51 m³·mol⁻¹ChemAxon
Polarizability14.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-8ba595019ef349f979472019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-4900000000-b4dd53a46d15401352512019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ll-9100000000-8befa79f3f4eed23fd002019-02-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0304376
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030902
KNApSAcK IDC00052891
Chemspider ID84004
KEGG Compound IDNot Available
BioCyc IDCPD-7619
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound93052
PDB IDNot Available
ChEBI ID32362
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]