Milk Composition Database: Showing metabocard for Isovaleric acid (BMDB0000718)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:26 UTC

Update Date

2020-06-04 20:31:42 UTC

MCDB ID

BMDB0000718

Secondary Accession Numbers

BMDB00718

Metabolite Identification

Common Name

Isovaleric acid

Description

3-Methylbutanoic acid, also known as isovalerate or 3-methylbutyrate, 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. 3-Methylbutanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 3-Methylbutanoic acid exists in all living species, ranging from bacteria to humans. 3-Methylbutanoic acid has been found to be associated with several diseases known as crohn's disease, ulcerative colitis, autism, and nonalcoholic fatty liver disease; also 3-methylbutanoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.

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

102.1317

Monoisotopic Molecular Weight

102.068079564

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 )

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-9e19eb5f5137b78591df	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-43967f1315b6b575f330	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-9e19eb5f5137b78591df	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-43967f1315b6b575f330	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-2825512cee017b3ab87c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-059f-9200000000-628e11f1ffbaa913ef57	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0gvo-9300000000-16b5d15d26810b72bb36	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-692791435c37fa74a692	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b4c1b59653cd4d803637	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b0f7e399edb7f95572ed	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-c8be68873f336c8de6d6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-63b09019c280c88ee64d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-63b09019c280c88ee64d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-871b21c20bba686fb915	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-6ce72c7a41bfb4bc1b2d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0nmi-9300000000-efcb74e7796ba9769f97	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e825f0aa9ab54c1695d3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-9ba126f982634fdc9406	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-afb863a56c8763c30251	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-244535e4070d536a29b3	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-9300000000-93ed2bc326380cb0d880	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-44b2fa11a5a6daab8dd0	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9000000000-f59a47a684453302cbed	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-83176e54a19e36af76f2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-81052c8b00621fcf0443	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-4c159e60dacc58e6ba98	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-7900000000-fd28737d49ed09628cfa	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2015-03-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	2 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	1.0 +/- 0.6 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.9 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	0.8 +/- 0.4 uM	Free fatty acid	PMID: 30994344	details

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

Synthesis Reference

Imada, Yukio; Mizuno, Sumiko; Mikawa, Takashi. Manufacture of isovaleric acid and 2-methylbutyric acid. Jpn. Kokai Tokkyo Koho (1986), 3 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Isovaleric acid (BMDB0000718)

Structure for BMDB0000718 (Isovaleric acid)