Cannabis Compound Database: Showing Compound Card for 3-Methyl butanoic acid (CDB005784)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Created at

2020-04-27 16:56:15 UTC

Updated at

2021-01-04 18:59:28 UTC

CannabisDB ID

CDB005784

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

3-Methyl butanoic acid

Description

Isovaleric acid, also known as 3-methylbutanoic acid or beta-methylbutyric acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Isovaleric acid is also classified as a fatty acid. It exists as a colorless liquid that is sparingly soluble in water. Isovaleric acid exists in all living species, ranging from bacteria to plants to humans. It is frequently found in a wide variety of plants and essential oils. Isovaleric acid has a strong pungent cheesy or sweaty smell. It is a major component of strong foot odor as it is produced by skin bacteria metabolizing leucine (PMID: 16699586 ). An excess of isovaleric acid in wine is generally seen as a defect, as it can give wines a sweaty, leathery, or barnyard-like smell. In wine, isovaleric acid is produced by the spoilage yeast Brettanomyces. In small amounts isovaleric acid can smell smokey, spicy, or medicinal. Isovaleric acid is found in many different plants and foods such as apples, bananas, roasted barley, beer, blackberry fruit, brandy, cheese, sour cherry, cinnamon, cider, citrus fruits, cocoa, coffee, cornmint plants, fish, grapes, hops, milk, mushrooms, papaya, passion fruit, peaches, pears, peanuts, peas, celery, safflower, yellow bell peppers, black pepper, raspberries, rosemary, strawberry, spearmint, tea, tomatoes and valerian root. It has been proposed that isovaleric acid is the anticonvulsant agent in valerian (PMID: 15509234 ). Isovaleric acid has been shown to be a a protein kinase A (PKA) agonist and causes smooth muscle relaxation via the PKA pathway (PMID: 30560338 ). Isovaleric acid (along with isovalerylcarnitine) is eleveated in the serum of patients with isovaleric acidemia. Isovaleric acidemia (IVA) is a rare autosomal recessive disorder of leucine metabolism caused by a defective isovaleryl-CoA dehydrogenase (IVD) gene (PMID: 32505769). Health problems related to isovaleric acidemia range from very mild to life-threatening. In severe cases, the features of isovaleric acidemia become apparent within a few days after birth. The initial symptoms include poor feeding, vomiting, seizures, and lack of energy (lethargy). These symptoms sometimes progress to more serious medical problems, including seizures, coma, and possibly death. A characteristic sign of isovaleric acidemia is a distinctive odor of sweaty feet during acute illness. Isovaleric acid is one of several acidic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Methyl-N-butyric acid	ChEBI
3-Methylbutanoic acid	ChEBI
3-Methylbuttersaeure	ChEBI
3-Methylbutyric acid	ChEBI
beta-Methylbutyric acid	ChEBI
Delphinic acid	ChEBI
Isobutylformic acid	ChEBI
Isopentanoic acid	ChEBI
Isopropylacetic acid	ChEBI
Isovalerate	ChEBI
Isovalerianic acid	ChEBI
Isovaleriansaeure	ChEBI
3-Methyl-N-butyrate	Generator
3-Methylbutanoate	Generator
3-Methylbutyrate	Generator
b-Methylbutyrate	Generator
b-Methylbutyric acid	Generator
beta-Methylbutyrate	Generator
Β-methylbutyrate	Generator
Β-methylbutyric acid	Generator
Delphinate	Generator
Isobutylformate	Generator
Isopentanoate	Generator
Isopropylacetate	Generator
Isovalerianate	Generator
3-Methyl butyric acid	HMDB
3-Methylbutyric acid: isopropyl-acetate	HMDB
3-Methylbutyric acid: isopropyl-acetic acid	HMDB
3-Methyl-1-butanoic acid	HMDB
Isovaleric acid	KEGG

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.13

Monoisotopic Molecular Weight

102.0681

IUPAC Name

3-methylbutanoic acid

Traditional Name

isovaleric acid

CAS Registry Number

503-74-2

SMILES

CC(C)CC(O)=O

InChI Identifier

InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)

InChI Key

GWYFCOCPABKNJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched 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

branched-chain saturated fatty acid (CHEBI:28484 )
short-chain fatty acid (CHEBI:28484 )
methylbutyric acid (CHEBI:28484 )
Branched fatty acids (C08262 )
Branched fatty acids (LMFA01020181 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Glycine max

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-29.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	40.7 mg/mL	Not Available
logP	1.16	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.26	ALOGPS
logP	1.21	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	5.01	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	2	ChemAxon
Refractivity	26.42 m³·mol⁻¹	ChemAxon
Polarizability	10.99 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)	splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9	2015-03-01	View Spectrum
GC-MS	3-Methyl butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-9e19eb5f5137b78591df	Spectrum
GC-MS	3-Methyl butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-43967f1315b6b575f330	Spectrum
GC-MS	3-Methyl butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-9e19eb5f5137b78591df	Spectrum
GC-MS	3-Methyl butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-43967f1315b6b575f330	Spectrum
Predicted GC-MS	3-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9000000000-2825512cee017b3ab87c	Spectrum
Predicted GC-MS	3-Methyl butanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-059f-9200000000-628e11f1ffbaa913ef57	Spectrum
Predicted GC-MS	3-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl butanoic 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)	splash10-0gvo-9300000000-16b5d15d26810b72bb36	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-692791435c37fa74a692	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b4c1b59653cd4d803637	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b0f7e399edb7f95572ed	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-c8be68873f336c8de6d6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-63b09019c280c88ee64d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-63b09019c280c88ee64d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-871b21c20bba686fb915	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-6ce72c7a41bfb4bc1b2d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0nmi-9300000000-efcb74e7796ba9769f97	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e825f0aa9ab54c1695d3	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-9ba126f982634fdc9406	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-afb863a56c8763c30251	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-244535e4070d536a29b3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-9300000000-93ed2bc326380cb0d880	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-44b2fa11a5a6daab8dd0	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9000000000-f59a47a684453302cbed	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-83176e54a19e36af76f2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-81052c8b00621fcf0443	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-4c159e60dacc58e6ba98	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-7900000000-fd28737d49ed09628cfa	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
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, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000718

DrugBank ID

DB03750

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Methylbutanoic acid

METLIN ID

109

PubChem Compound

10430

PDB ID

Not Available

ChEBI ID

28484

References

General References

Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. doi: 10.1139/w05-130. [PubMed:16699586 ]
Eadie MJ: Could valerian have been the first anticonvulsant? Epilepsia. 2004 Nov;45(11):1338-43. doi: 10.1111/j.0013-9580.2004.27904.x. [PubMed:15509234 ]
Blakeney BA, Crowe MS, Mahavadi S, Murthy KS, Grider JR: Branched Short-Chain Fatty Acid Isovaleric Acid Causes Colonic Smooth Muscle Relaxation via cAMP/PKA Pathway. Dig Dis Sci. 2019 May;64(5):1171-1181. doi: 10.1007/s10620-018-5417-5. Epub 2018 Dec 17. [PubMed:30560338 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Showing Compound Card for 3-Methyl butanoic acid (CDB005784)

Structure for CDB005784 (3-Methyl butanoic acid)

Enzymes