Cannabis Compound Database: Showing Compound Card for Octanoic acid (CDB005769)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (3)transporters (3) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-27 16:54:09 UTC

Updated at

2021-01-22 17:44:17 UTC

CannabisDB ID

CDB005769

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Octanoic acid

Description

Octanoic acid, also known by caprylic acid has the molecular formula of C8H16O2. It appears as a colorless to light yellow liquid with a mild odor. Octanoic acid is soluble in most organic solvents and in dilute nitric acid. Octanoic acid is industrially used to make esters for perfumes and fruit flavors and as an intermediate for food-grade additives. Octanoic acid is an 8 carbon atoms long, straight-chain, saturated fatty acid. Caprylic 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. Octanoic acid is volatilized during the combustion of cannabis and can be found in cannabis smoke (Ref: Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Heptanecarboxylic acid	ChEBI
8:0	ChEBI
Acide octanoique	ChEBI
Acido octanoico	ChEBI
Acidum octanocium	ChEBI
Acidum octanoicum	ChEBI
C8:0	ChEBI
CH3-[CH2]6-COOH	ChEBI
Kaprylsaeure	ChEBI
N-Caprylic acid	ChEBI
N-Octanoic acid	ChEBI
N-Octoic acid	ChEBI
N-Octylic acid	ChEBI
OCTANOIC ACID (caprylIC ACID)	ChEBI
Octansaeure	ChEBI
Octoic acid	ChEBI
Octylic acid	ChEBI
Octanoate	Kegg
1-Heptanecarboxylate	Generator
N-Caprylate	Generator
N-Octanoate	Generator
N-Octoate	Generator
N-Octylate	Generator
OCTANOate (caprylate)	Generator
Octoate	Generator
Octylate	Generator
Octanoic acid	Generator
Caprylate	Generator
Emery 657	HMDB
Kortacid 0899	HMDB
Lunac 8-95	HMDB
Lunac 8-98	HMDB
Neo-fat 8	HMDB
Neo-fat 8S	HMDB
Prifac 2901	HMDB
Caprylic acid, cadmium salt	HMDB
Caprylic acid, cesium salt	HMDB
Caprylic acid, manganese salt	HMDB
Caprylic acid, nickel(+2) salt	HMDB
Caprylic acid, zinc salt	HMDB
Caprylic acid, aluminum salt	HMDB
Caprylic acid, barium salt	HMDB
Caprylic acid, chromium(+2) salt	HMDB
Caprylic acid, lead(+2) salt	HMDB
Caprylic acid, potassium salt	HMDB
Caprylic acid, tin(+2) salt	HMDB
Sodium octanoate	HMDB
Caprylic acid, 14C-labeled	HMDB
Caprylic acid, lithium salt	HMDB
Caprylic acid, ruthenium(+3) salt	HMDB
Caprylic acid, sodium salt	HMDB
Caprylic acid, sodium salt, 11C-labeled	HMDB
Caprylic acid, tin salt	HMDB
Caprylic acid, zirconium salt	HMDB
Sodium caprylate	HMDB
Caprylic acid, ammonia salt	HMDB
Caprylic acid, calcium salt	HMDB
Caprylic acid, cobalt salt	HMDB
Caprylic acid, copper salt	HMDB
Caprylic acid, copper(+2) salt	HMDB
Caprylic acid, iridum(+3) salt	HMDB
Caprylic acid, iron(+3) salt	HMDB
Caprylic acid, lanthanum(+3) salt	HMDB
Caprylic acid, zirconium(+4) salt	HMDB
FA(8:0)	HMDB
Lithium octanoate	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.21

Monoisotopic Molecular Weight

144.115

IUPAC Name

octanoic acid

Traditional Name

caprylic acid

CAS Registry Number

68937-74-6

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)

InChI Key

WWZKQHOCKIZLMA-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:28837 )
straight-chain saturated fatty acid (CHEBI:28837 )
Straight chain fatty acids (C06423 )
Saturated fatty acids (C06423 )
Straight chain fatty acids (LMFA01010008 )

Ontology

Physiological effect

Health effect:

Health condition:

Sudden death

Metabolism and nutrition disorders:

Hypoglycemia

Gastrointestinal disorders:

Vomiting

Nervous system disorders:

Lethargy

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Biological role:

Industrial application:

Household products:

Antimicrobial agent:

Antibacterial

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	16.5 °C	Not Available
Boiling Point	239.7 °C	Wikipedia
Water Solubility	0.79 mg/mL	Not Available
logP	3.05	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.92	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.19	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	6	ChemAxon
Refractivity	40.28 m³·mol⁻¹	ChemAxon
Polarizability	17.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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)	splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c	2014-09-20	View Spectrum
GC-MS	Octanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-e609d5de69ede6fbcde0	Spectrum
GC-MS	Octanoic acid, 1 TMS, GC-MS Spectrum	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	Spectrum
GC-MS	Octanoic acid, non-derivatized, GC-MS Spectrum	splash10-03kc-9000000000-74cfce03769b41313952	Spectrum
GC-MS	Octanoic acid, non-derivatized, GC-MS Spectrum	splash10-0uyi-0931100000-7668e36e436054042b5c	Spectrum
GC-MS	Octanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0910000000-e609d5de69ede6fbcde0	Spectrum
GC-MS	Octanoic acid, non-derivatized, GC-MS Spectrum	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	Spectrum
GC-MS	Octanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-0910000000-9ecb4ccb46e89710f76a	Spectrum
Predicted GC-MS	Octanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0596-9100000000-8854c56056d8d3405087	Spectrum
Predicted GC-MS	Octanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-062l-9100000000-67da39159980b9078fab	Spectrum
Predicted GC-MS	Octanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Octanoic 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, Negative (Annotated)	splash10-0006-0900000000-bb237630bedcee6145d1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-2900000000-98284f50a271878c8481	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-5900000000-209fbbacd4996b9a770d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03kc-9000000000-74cfce03769b41313952	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e2c4dff10393086340f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-bbde8564b4e5543a636a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negative	splash10-0006-0900000000-d219a0c6559a4783fd81	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-e2c4dff10393086340f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-bbde8564b4e5543a636a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-0900000000-ca22ecd0b25fa371fc73	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0gvp-9100000000-58c00a2024ba0bae4ff4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-2505e6738cf5d5877654	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-1ab4cdf8f74c93312743	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-ac7c80e50c93b8cc3af7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9400000000-d2694b5f89d8eaeb2ab1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-f2b24072c91d8b0e4078	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-ad62d44e72f4dd1760ab	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-7900000000-9c869b84815f21dffc7c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-b8a648d443695914e479	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6u-9100000000-f5c38fdad70b324e75ac	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-bee103956686b4840d1e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-e7cbd036c8e80018c825	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8f2b048da6331570976c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-cd31ca01a5fa6be86acb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-682c215be5abe1fe87ed	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Beta Oxidation of Very Long Chain Fatty Acids
Fatty Acid Biosynthesis		Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		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
Solute carrier family 22 member 11	SLC22A11	11q13.1	Q9NSA0	details
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	3p21.31	O43772	details
Solute carrier family 22 member 6	SLC22A6	11q12.3	Q4U2R8	details

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000482

DrugBank ID

DB04519

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28837

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. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

Enzyme Details

2. 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

3. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

Showing Compound Card for Octanoic acid (CDB005769)

Structure for CDB005769 (Octanoic acid)

Enzymes

Transporters