Cannabis Compound Database: Showing Compound Card for Decanoic acid (CDB005775)

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Record Information

Version

1.0

Created at

2020-04-27 16:55:21 UTC

Updated at

2021-01-22 17:44:17 UTC

CannabisDB ID

CDB005775

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Decanoic acid

Description

Decanoic acid, also known by capric acid has the molecular formula of C10H20O2. Decanoic acid is a white crystalline solid with a rancid odor and a melting point of 31.5°C. Soluble in most organic solvents and in dilute nitric acid. Decanoic acid is industrially used to make esters for perfumes and fruit flavors and as an intermediate for food-grade additives. Decanoic acid is a 10 carbon atoms long, straight-chain, saturated fatty acid. It has been described as an antibacterial agent, an anti-inflammatory agent, a human metabolite, a volatile oil component, a plant metabolite and an algal metabolite. It is the conjugate acid of a decanoate. Capric acid is found naturally in the coconut and palm kernel oils as well as the milk of various mammals. It is widespread in plant oils and as glycerides in seed oils. Decanoic acid is volatilized during the combustion of cannabis and can be found in cannabis smoke (Ref: Ref:DOI ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Nonanecarboxylic acid	ChEBI
10:0	ChEBI
C10:0	ChEBI
Caprinic acid	ChEBI
CH3-[CH2]8-COOH	ChEBI
Decanoate	ChEBI
Decoic acid	ChEBI
Decylic acid	ChEBI
Dekansaeure	ChEBI
Kaprinsaeure	ChEBI
N-Capric acid	ChEBI
N-Decanoic acid	ChEBI
N-Decoic acid	ChEBI
N-Decylic acid	ChEBI
1-Nonanecarboxylate	Generator
Caprinate	Generator
Decanoic acid	Generator
Decoate	Generator
Decylate	Generator
N-Caprate	Generator
N-Decanoate	Generator
N-Decoate	Generator
N-Decylate	Generator
Caprate	Generator
Caprynate	HMDB
Caprynic acid	HMDB
Emery 659	HMDB
Lunac 10-95	HMDB
Lunac 10-98	HMDB
Prifac 2906	HMDB
Prifac 296	HMDB
Decanoic acid, sodium salt	HMDB
Sodium caprate	HMDB
Sodium decanoate	HMDB
FA(10:0)	HMDB

Chemical Formula

C₁₀H₂₀O₂

Average Molecular Weight

172.26

Monoisotopic Molecular Weight

172.1463

IUPAC Name

decanoic acid

Traditional Name

capric acid

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)

InChI Key

GHVNFZFCNZKVNT-UHFFFAOYSA-N

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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:30813 )
straight-chain saturated fatty acid (CHEBI:30813 )
Straight chain fatty acids (C01571 )
Saturated fatty acids (C01571 )
Straight chain fatty acids (LMFA01010010 )

Ontology

Physiological effect

Health effect:

Health condition:

Sudden death

Metabolism and nutrition disorders:

Hypoglycemia

Gastrointestinal disorders:

Vomiting

Nervous system disorders:

Lethargy

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	31.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.062 mg/mL	Not Available
logP	4.09	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	3.93	ALOGPS
logP	3.59	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	49.48 m³·mol⁻¹	ChemAxon
Polarizability	21.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-bf788cb34c09c6af56bf	2014-09-20	View Spectrum
GC-MS	Decanoic acid, 1 TMS, GC-MS Spectrum	splash10-017i-2920000000-7f6721f01b80a790d544	Spectrum
GC-MS	Decanoic acid, non-derivatized, GC-MS Spectrum	splash10-076u-9000000000-96a2e9e00e464db3c086	Spectrum
GC-MS	Decanoic acid, non-derivatized, GC-MS Spectrum	splash10-017i-2920000000-7f6721f01b80a790d544	Spectrum
GC-MS	Decanoic acid, non-derivatized, GC-MS Spectrum	splash10-016r-1910000000-1cc1026f6f325d994ab4	Spectrum
Predicted GC-MS	Decanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052g-9200000000-71a57b0e200e46fb66ed	Spectrum
Predicted GC-MS	Decanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g0-9300000000-c615f39c0b907a00f67c	Spectrum
Predicted GC-MS	Decanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Decanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-0a7f944302bce161f7e5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00b9-1900000000-b68efbceecf3433a9995	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-005a-9600000000-f2a54ed1a56ee9b7af77	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-076u-9000000000-96a2e9e00e464db3c086	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0900000000-771e7907916bf05e6b10	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-0900000000-f1e000384728ee06f802	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-1900000000-42a901bb54546da030da	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-83e77de04461ded1c4bc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-f3190b828218d04d3cc7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0000000910-e82208ed71b4a3735258	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-00di-0900000000-8c6cdf0491f51ba6ef26	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-856f34ef153b15cb3d1d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-4900000000-efb0bd73973bf0c317fd	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d81148541fa575d32552	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-99cd0519b210c46b4a4c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmi-1900000000-209285ec682ca47e1e5d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-fb697080d761d0f48fe2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-856f34ef153b15cb3d1d	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-4900000000-efb0bd73973bf0c317fd	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d81148541fa575d32552	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-99cd0519b210c46b4a4c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmi-1900000000-209285ec682ca47e1e5d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-fb697080d761d0f48fe2	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Beta Oxidation of Very Long Chain Fatty Acids
Fatty Acid Biosynthesis		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Peroxisomal carnitine O-octanoyltransferase	CROT	7q21.1	Q9UKG9	details
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	1p32	P23786	details
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	3p21.31	O43772	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	3p21.31	O43772	details
Glycolipid transfer protein	GLTP	12q24.11	Q9NZD2	details

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000511

DrugBank ID

DB03600

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Decanoic acid

METLIN ID

336

PubChem Compound

2969

PDB ID

Not Available

ChEBI ID

30813

References

General References

Not Available

Enzymes

Enzyme Details

1. Peroxisomal carnitine O-octanoyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:: CROT
Uniprot ID:: Q9UKG9
Molecular weight:: 10213.63

Enzyme Details

2. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: P23786
Molecular weight:: 73776.335

Enzyme Details

3. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Transporters

Enzyme Details

1. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Enzyme Details

2. Glycolipid transfer protein

General function:: Involved in glycolipid transporter activity
Specific function:: Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides
Gene Name:: GLTP
Uniprot ID:: Q9NZD2
Molecular weight:: 23849.6

Showing Compound Card for Decanoic acid (CDB005775)

Structure for CDB005775 (Decanoic acid)

Enzymes

Transporters