Showing Compound Card for Caprylic acid (CDB000382)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-03-19 00:34:06 UTC
Updated at2020-11-18 16:35:08 UTC
CannabisDB IDCDB000382
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCaprylic acid
DescriptionCaprylic acid, or octanoic acid, with the structural formula CH3(CH2)6CO2H, is an eight-carbon straight-chain fatty acid and a carboxylic acid. It is an oily liquid with a slightly unpleasant rancid taste and odor. It is minimally soluble in water. Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, shallots, coconuts and breast milk. Caprylic acid is straight-chain fatty acids found in cannabis (PMID: 6991645 ). Caprylic acid is taken as a dietary supplement. Caprylic acid is used commercially in the production of esters used in perfumery and in the manufacture of dyes. Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, industrial facilities, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in greenhouses and garden centers. Caprylic acid, and other fatty acids, affect the hunger hormone ghrelin. Ghrelin must be acylated, where it acquires an -OH group, before it can stimulate the hunger receptors in the hypothalamus. Caprylic acid becomes linked post-translationally to serine at the 3-position by the enzyme ghrelin O-acyltransferase (GOAT), located on the cell membrane of ghrelin cells in the stomach and pancreas (PMID 19896496 ). Caprylic acid affects those with medium-chain acyl-CoA dehydrogenase deficiency (MCAD), which is an inborn error of metabolism, marked by mutations of the gene ACADM. Those affected with MCAD have difficulties converting fatty acids to energy, especially during fasting. As a result, fatty acids build up and cause damage to liver and brain (PMID: 27536022 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-HeptanecarboxylateChEBI
CaprilateChEBI
CaprylateChEBI
CH3-[CH2]6-COO(-)ChEBI
N-CaprylateChEBI
N-OctanoateChEBI
N-OctoateChEBI
N-OctylateChEBI
Octanoic acid, ion(1-)ChEBI
OctylateChEBI
1-Heptanecarboxylic acidGenerator
Caprilic acidGenerator
Caprylic acidGenerator
N-Caprylic acidGenerator
N-Octanoic acidGenerator
N-Octoic acidGenerator
N-Octylic acidGenerator
Octanoate, ion(1-)Generator
Octylic acidGenerator
Octanoic acidGenerator
Caprylic acid, 14C-labeledMeSH
Caprylic acid, aluminum saltMeSH
Caprylic acid, ammonia saltMeSH
Caprylic acid, barium saltMeSH
Caprylic acid, cadmium saltMeSH
Caprylic acid, calcium saltMeSH
Caprylic acid, cesium saltMeSH
Caprylic acid, chromium(+2) saltMeSH
Caprylic acid, cobalt saltMeSH
Caprylic acid, copper saltMeSH
Caprylic acid, copper(+2) saltMeSH
Caprylic acid, iridum(+3) saltMeSH
Caprylic acid, iron(+3) saltMeSH
Caprylic acid, lanthanum(+3) saltMeSH
Caprylic acid, lead(+2) saltMeSH
Caprylic acid, lithium saltMeSH
Caprylic acid, manganese saltMeSH
Caprylic acid, nickel(+2) saltMeSH
Caprylic acid, potassium saltMeSH
Caprylic acid, ruthenium(+3) saltMeSH
Caprylic acid, sodium saltMeSH
Caprylic acid, sodium salt, 11C-labeledMeSH
Caprylic acid, tin saltMeSH
Caprylic acid, tin(+2) saltMeSH
Caprylic acid, zinc saltMeSH
Caprylic acid, zirconium saltMeSH
Caprylic acid, zirconium(+4) saltMeSH
Lithium octanoateMeSH
Sodium caprylateMeSH
Sodium octanoateMeSH
Chemical FormulaC8H15O2
Average Molecular Weight143.2
Monoisotopic Molecular Weight143.1072
IUPAC Nameoctanoate
Traditional Nameoctanoate
CAS Registry Number74-81-7
SMILES
CCCCCCCC([O-])=O
InChI Identifier
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1
InChI KeyWWZKQHOCKIZLMA-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 Point16.7 °CWikipedia
Boiling Point239.7 °CWikipedia
Water Solubility0.068 g/100 mLWikipedia
logP3.05Wikipedia
Predicted Properties
PropertyValueSource
logP3.01ALOGPS
logP2.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.11 m³·mol⁻¹ChemAxon
Polarizability16.95 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, Positivesplash10-002f-2900000000-755179c9d14d1bbb77ec2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-9800000000-9285cc5963f767a994c32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-06a4c61d4c63d78974632016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-c8005ce6014073d81b472016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-6900000000-f6abffe9512a2dfa8afe2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9200000000-df94975221001b91f2332016-09-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Ghrelin O-acyltransferaseMBOAT48p12Q96T53 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0304443
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031069
KNApSAcK IDC00035613
Chemspider ID106634
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound119389
PDB IDNot Available
ChEBI ID25646
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 ]
  2. Castaneda TR, Tong J, Datta R, Culler M, Tschop MH: Ghrelin in the regulation of body weight and metabolism. Front Neuroendocrinol. 2010 Jan;31(1):44-60. doi: 10.1016/j.yfrne.2009.10.008. Epub 2009 Nov 5. [PubMed:19896496 ]
  3. Vishwanath VA: Fatty Acid Beta-Oxidation Disorders: A Brief Review. Ann Neurosci. 2016 Mar;23(1):51-5. doi: 10.1159/000443556. Epub 2016 Mar 11. [PubMed:27536022 ]

Enzymes

Enzyme Details
1. Ghrelin O-acyltransferase
General function:
serine O-acyltransferase activity
Specific function:
Mediates the octanoylation of ghrelin at 'Ser-3'. Can use a variety of fatty acids as substrates including octanoic acid, decanoic acid and tetradecanoic acid.
Gene Name:
MBOAT4
Uniprot ID:
Q96T53
Molecular weight:
49715.51