Cannabis Compound Database: Showing Compound Card for Capric acid (CDB000384)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1)transporters (2) Show 7 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:34:13 UTC

Updated at

2020-11-18 16:35:08 UTC

CannabisDB ID

CDB000384

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Capric acid

Description

Capric acid, with the molecular formula CH3(CH2)8COOH, also known as Decanoic acid (C10:0) or decylic acid, 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. Capric Acid is a saturated medium-chain fatty acid with a 10-carbon backbone. Capric acid has a sweaty, unpleasant odor. Capric Acid is one of several saturated fatty acids that are known in cannabis plants (PMID:6991645 ). Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%). It is found in the milk of various mammals and to a lesser extent in other animal fats ( Ref:DOI ). It also comprises 1.62% of the fats from the fruit of the durian species Durio graveolens. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric acid acts as a non-competitive Œ±-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPA) receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner and it exhibits anti-seizure effects (PMID: 26608744 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Nonanecarboxylate	ChEBI
Caprate	ChEBI
Caprinate	ChEBI
Caprynate	ChEBI
CH3-[CH2]8-COO(-)	ChEBI
Decanoic acid anion	ChEBI
Decoate	ChEBI
Decylate	ChEBI
N-Caprate	ChEBI
N-Decanoate	ChEBI
N-Decoate	ChEBI
N-Decylate	ChEBI
NC9H19CO2 Anion	ChEBI
1-Nonanecarboxylic acid	Generator
Capric acid	Generator
Caprinic acid	Generator
Caprynic acid	Generator
Decanoate anion	Generator
Decoic acid	Generator
Decylic acid	Generator
N-Capric acid	Generator
N-Decanoic acid	Generator
N-Decoic acid	Generator
N-Decylic acid	Generator
Decanoic acid (N-C10:0)	Generator
Decanoic acid	Generator

Chemical Formula

C₁₀H₁₉O₂

Average Molecular Weight

171.26

Monoisotopic Molecular Weight

171.1385

IUPAC Name

decanoate

Traditional Name

decanoate

CAS Registry Number

334-48-5

SMILES

CCCCCCCCCC([O-])=O

InChI Identifier

InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)/p-1

InChI Key

GHVNFZFCNZKVNT-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid anion (CHEBI:27689 )
straight-chain saturated fatty acid anion (CHEBI:27689 )
fatty acid anion 10:0 (CHEBI:27689 )
a medium chain fatty acid (CPD-3617 )
a saturated fatty acid (CPD-3617 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	31.6 °C	Wikipedia
Boiling Point	268.7 °C	Wikipedia
Water Solubility	0.015 g/100 mL at 20 °C	Wikipedia
logP	4.09	Wikipedia

Predicted Properties

Property	Value	Source
logP	4.13	ALOGPS
logP	3.59	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	60.31 m³·mol⁻¹	ChemAxon
Polarizability	21.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0900000000-67cf1821fc2df55ba202	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05i0-3900000000-6f2f9769d9492f327db8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-087b2ae66190f2919c8b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-48510a5111ef48546f71	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-0900000000-21561f718199fa548131	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-6900000000-92aba5152a727532bd78	2015-09-15	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glutamate receptor 1	GRIA1	5q33\|5q31.1	P42261	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glutamate receptor 1	GRIA1	5q33\|5q31.1	P42261	details
Glutamate receptor 2	GRIA2	4q32-q33	P42262	details

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glutamate receptor 1	GRIA1	5q33\|5q31.1	P42261	details
Glutamate receptor 2	GRIA2	4q32-q33	P42262	details
Glutamate receptor 3	GRIA3	Xq25-q26	P42263	details
Glutamate receptor 4	GRIA4	11q22	P48058	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-3617

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4678093

PDB ID

Not Available

ChEBI ID

27689

References

General References

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 ]
Chang P, Augustin K, Boddum K, Williams S, Sun M, Terschak JA, Hardege JD, Chen PE, Walker MC, Williams RS: Seizure control by decanoic acid through direct AMPA receptor inhibition. Brain. 2016 Feb;139(Pt 2):431-43. doi: 10.1093/brain/awv325. Epub 2015 Nov 25. [PubMed:26608744 ]

Enzymes

Enzyme Details

1. Glutamate receptor 1

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:: GRIA1
Uniprot ID:: P42261
Molecular weight:: 101505.2

Transporters

Enzyme Details

1. Glutamate receptor 1

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:: GRIA1
Uniprot ID:: P42261
Molecular weight:: 101505.2

Enzyme Details

2. Glutamate receptor 2

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:: GRIA2
Uniprot ID:: P42262
Molecular weight:: 98820.3

Showing Compound Card for Capric acid (CDB000384)

Structure for CDB000384 (Capric acid)

Enzymes

Transporters