Cannabis Compound Database: Showing Compound Card for Caproic acid (CDB000380)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (10)transporters (1) Show 18 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:34:00 UTC

Updated at

2020-12-07 19:07:24 UTC

CannabisDB ID

CDB000380

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Caproic acid

Description

Caproic acid, also known as hexanoate or caproate, 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. Caproic acid is a medium chain triglyceride (MCT). Caproic acid is a medium chain triglycerides (MCT). Caproic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It is a conjugate acid of a hexanoate. Caproic acid is found naturally in various plant and animal fats and oils. Caproic acid is one of the saturated fatty acids that are known in cannabis plant. (PMID: 6991645 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexanoic acid	ChEBI
1-Pentanecarboxylic acid	ChEBI
6:0	ChEBI
Butylacetic acid	ChEBI
C6:0	ChEBI
Capronic acid	ChEBI
CH3-[CH2]4-COOH	ChEBI
Hexanoate	ChEBI
Hexoic acid	ChEBI
Hexylic acid	ChEBI
N-Caproic acid	ChEBI
N-Hexanoic acid	ChEBI
N-Hexoic acid	ChEBI
N-Hexylic acid	ChEBI
Pentanecarboxylic acid	ChEBI
Pentiformic acid	ChEBI
Pentylformic acid	ChEBI
1-Hexanoate	Generator
1-Pentanecarboxylate	Generator
Butylacetate	Generator
Capronate	Generator
Hexanoic acid	Generator
Hexoate	Generator
Hexylate	Generator
N-Caproate	Generator
N-Hexanoate	Generator
N-Hexoate	Generator
N-Hexylate	Generator
Pentanecarboxylate	Generator
Pentiformate	Generator
Pentylformate	Generator
Caproate	Generator
Hexanoic acid, calcium salt	MeSH, HMDB
Hexanoic acid, sodium salt, 1-(11)C-labeled	MeSH, HMDB
Hexanoic acid, nickel (2+) salt	MeSH, HMDB
Hexanoic acid, sodium salt	MeSH, HMDB
Bismuth(III)hexanoate	MeSH, HMDB
Hexanoic acid, copper (2+) salt	MeSH, HMDB
Hexanoic acid, manganese (2+) salt	MeSH, HMDB
Bi(ohex)3	MeSH, HMDB
Hexanoic acid, barium salt	MeSH, HMDB
Hexanoic acid, potassium salt	MeSH, HMDB
Hexanoic acid, rhodium (2+) salt	MeSH, HMDB
FA(6:0)	HMDB
Calcium N-hexanoate	MeSH, HMDB
Hexanoic acid, sodium salt (1:1)	MeSH, HMDB
Sodium capronate	MeSH, HMDB
Calcium hexanoate	MeSH, HMDB
Caproic acid sodium salt	MeSH, HMDB
Sodium caproate	MeSH, HMDB
Sodium hexanoate	MeSH, HMDB

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.16

Monoisotopic Molecular Weight

116.0837

IUPAC Name

hexanoic acid

Traditional Name

hexanoic acid

CAS Registry Number

142-62-1

SMILES

CCCCCC(O)=O

InChI Identifier

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

InChI Key

FUZZWVXGSFPDMH-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:30776 )
straight-chain saturated fatty acid (CHEBI:30776 )
Straight chain fatty acids (C01585 )
Saturated fatty acids (C01585 )
Straight chain fatty acids (LMFA01010006 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	−3.4 °C	Wikipedia
Boiling Point	205.8 °C	Wikipedia
Water Solubility	10.3 mg/mL	Not Available
logP	1.92	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.88	ALOGPS
logP	1.81	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	5.09	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	4	ChemAxon
Refractivity	31.07 m³·mol⁻¹	ChemAxon
Polarizability	13.27 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)	splash10-03di-9000000000-fe3fab44832ddab1082e	2014-09-20	View Spectrum
GC-MS	Caproic acid, 1 TMS, GC-MS Spectrum	splash10-00yi-3900000000-8d7942410dfae70c7c9d	Spectrum
GC-MS	Caproic acid, non-derivatized, GC-MS Spectrum	splash10-03di-9000000000-f4bf00b677d90d54ba69	Spectrum
GC-MS	Caproic acid, non-derivatized, GC-MS Spectrum	splash10-00yi-3900000000-8d7942410dfae70c7c9d	Spectrum
Predicted GC-MS	Caproic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-9ee618fa3c0bd9d56748	Spectrum
Predicted GC-MS	Caproic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9200000000-be939d8c0455d1af93a6	Spectrum
Predicted GC-MS	Caproic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Caproic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Caproic 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)	splash10-014i-0900000000-ba8c7078846c268d61a6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-03di-0900000000-151d5971be58b6799d2e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-02t9-1900000000-36096ef7dfebaa193910	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03di-9000000000-f4bf00b677d90d54ba69	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-5013166dd3b692762812	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-5900000000-52b3e7f8b01498621772	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-e3af905666760ff49069	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-5013166dd3b692762812	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-5900000000-52b3e7f8b01498621772	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e3af905666760ff49069	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-01b9-6900000000-763e9a8e0f15e13fae3c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-df670aaa002d77689cc7	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9700000000-5489131065e0934751a7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-9100000000-68f7c2883fb339578ace	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-8e5e925d60baa2f176c2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e877f22e42e8323f59e3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9800000000-b5d583466919719819a1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-791ecce51d7cdde8f0f5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05tg-9000000000-b176d73a7b4fabde1ad4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-08e066ae069da04a8689	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-808b7302aa744c7a1c20	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-3e67c250e6a67f63a0dd	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, 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
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)		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
Acyl-coenzyme A synthetase ACSM1, mitochondrial	ACSM1	16p12.3	Q08AH1	details
Acyl-coenzyme A synthetase ACSM6, mitochondrial	ACSM6	10q23.33	Q6P461	details
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	ACSM2A	16p12.3	Q08AH3	details
Acyl-coenzyme A synthetase ACSM2B, mitochondrial	ACSM2B	16p12.3	Q68CK6	details
Acyl-coenzyme A synthetase ACSM3, mitochondrial	ACSM3	16p13.11	Q53FZ2	details
Acyl-coenzyme A synthetase ACSM5, mitochondrial	ACSM5	16p12.3	Q6NUN0	details
Acyl-coenzyme A synthetase ACSM4, mitochondrial	ACSM4	12p13.31	P0C7M7	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Mitochondrial carnitine/acylcarnitine carrier protein	SLC25A20	3p21.31	O43772	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acyl-coenzyme A synthetase ACSM1, mitochondrial	ACSM1	16p12.3	Q08AH1	details
Acyl-coenzyme A synthetase ACSM6, mitochondrial	ACSM6	10q23.33	Q6P461	details
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	ACSM2A	16p12.3	Q08AH3	details
Acyl-coenzyme A synthetase ACSM2B, mitochondrial	ACSM2B	16p12.3	Q68CK6	details
Acyl-coenzyme A synthetase ACSM3, mitochondrial	ACSM3	16p13.11	Q53FZ2	details
Acyl-coenzyme A synthetase ACSM5, mitochondrial	ACSM5	16p12.3	Q6NUN0	details
Acyl-coenzyme A synthetase ACSM4, mitochondrial	ACSM4	12p13.31	P0C7M7	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000535

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hexanoic_acid

METLIN ID

5520

PubChem Compound

8892

PDB ID

Not Available

ChEBI ID

30776

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 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Show All

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

Enzyme Details

4. Acyl-coenzyme A synthetase ACSM1, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:: ACSM1
Uniprot ID:: Q08AH1
Molecular weight:: 65272.74

Enzyme Details

5. Acyl-coenzyme A synthetase ACSM6, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ACSM6
Uniprot ID:: Q6P461
Molecular weight:: 53584.545

Enzyme Details

6. Acyl-coenzyme A synthetase ACSM2A, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM2A
Uniprot ID:: Q08AH3
Molecular weight:: 64223.7

Enzyme Details

7. Acyl-coenzyme A synthetase ACSM2B, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:: ACSM2B
Uniprot ID:: Q68CK6
Molecular weight:: 64270.78

Enzyme Details

8. Acyl-coenzyme A synthetase ACSM3, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM3
Uniprot ID:: Q53FZ2
Molecular weight:: 66152.235

Enzyme Details

9. Acyl-coenzyme A synthetase ACSM5, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM5
Uniprot ID:: Q6NUN0
Molecular weight:: 64759.55

Enzyme Details

10. Acyl-coenzyme A synthetase ACSM4, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:: ACSM4
Uniprot ID:: P0C7M7
Molecular weight:: 65702.225

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

Only showing the first 10 proteins. There are 18 proteins in total.

Show All

Showing Compound Card for Caproic acid (CDB000380)

Structure for CDB000380 (Caproic acid)

Enzymes

Transporters