P. aeruginosa Metabolome Database: a-Ketoisovaleric acid (PAMDB000004)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000004

Identification

Name:

a-Ketoisovaleric acid

Description:

a-Ketoisovaleric acid is a precursor of valine, leucine and pantothenate. It can be synthesized in Pseudomonas aeruginosa. anabolically (via dihydroxyacid dehydrase) and catabolically (branched-chain amino acid transaminase and alanine-valine transaminase)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Keto-3-Methylbutyrate
2-Keto-3-Methylbutyric acid
2-Ketoisovalerate
2-Ketoisovaleric acid
2-Oxo-3-methylbutanoate
2-Oxo-3-methylbutanoic acid
2-Oxo-3-methylbutyrate
2-Oxo-3-methylbutyric acid
2-Oxoisovalerate
2-Oxoisovaleric acid
3-Methyl-2-oxo-Butanoate
3-Methyl-2-oxo-Butanoic acid
3-Methyl-2-oxo-Butyrate
3-Methyl-2-oxo-Butyric acid
3-Methyl-2-oxobutanoate
3-Methyl-2-oxobutanoic acid
3-Methyl-2-oxobutyrate
3-Methyl-2-oxobutyric acid
A-Keto-b-Methylbutyrate
a-Keto-b-Methylbutyric acid
A-Keto-Isovalerate
a-Keto-Isovaleric acid
A-Ketoisovalerate
A-Oxo-b-methylbutyrate
a-Oxo-b-methylbutyric acid
A-Oxoisovalerate
a-Oxoisovaleric acid
alpha-Ketoisovalerate
alpha-Ketoisovaleric acid
Dimethylpyruvate
Dimethylpyruvic acid
Isopropylglyoxylate
Isopropylglyoxylic acid
Ketovaline
α-Ketoisovalerate
α-Ketoisovaleric acid

Chemical Formula:

C₅H₈O₃

Average Molecular Weight:

116.1152

Monoisotopic Molecular Weight:

116.047344122

InChI Key:

QHKABHOOEWYVLI-UHFFFAOYSA-N

InChI:

InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)

CAS number:

759-05-7

IUPAC Name:

3-methyl-2-oxobutanoic acid

Traditional IUPAC Name:

α-ketoisovalerate

SMILES:

CC(C)C(=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Methyl-branched fatty acid
Short-chain keto acid
Branched fatty acid
Fatty acyl
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:16530 )
Branched fatty acids (C00141 )
Branched fatty acids (LMFA01020274 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

31.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	0.1 g/mL MeOH hot clear	PhysProp
LogP:	0.329	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	30.2 mg/mL	ALOGPS
logP	0.49	ALOGPS
logP	1.31	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	27.19 m³·mol^-1	ChemAxon
Polarizability	11.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Metabolic pathways pae01100
Pantothenate and CoA biosynthesis pae00770
Pyruvate metabolism pae00620
Valine, leucine and isoleucine biosynthesis pae00290
Valine, leucine and isoleucine degradation pae00280

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-000i-9500000000-ff936b879a69b5d118f8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-000i-8920000000-e37b37d64d43dcf763f0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9400000000-e3995acc4818a98d0f48	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0f79-9720000000-5d89487273e44ea61a68	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-10ab58a33e9ca7dbace0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-ad51ff01c94b6046ad64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-9993174a7b1801b90ddb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00xr-9500000000-293818b81e0879b6feb2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-75058f27a2178b9cf121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-4c20af39e8ee009d5278	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-9400000000-21f8c3fae79161c82099	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-5f25e41413738bb6b5d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-801af00dea93fcfd637d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-8900000000-5185c7dfc72c25069904	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9200000000-7e2a275a65197f96f5d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0600-9000000000-0013e0ff06f9896a1337	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available

References

References:

Chuang DT, Niu WL, Cox RP: Activities of branched-chain 2-oxo acid dehydrogenase and its components in skin fibroblasts from normal and classical-maple-syrup-urine-disease subjects. Biochem J. 1981 Oct 15;200(1):59-67. Pubmed: 6895847
Gallina DL, Dominguez JM, Hoschoian JC, Barrio JR: Maintenance of nitrogen balance in a young woman by substitution of -ketoisovaleric acid for valine. J Nutr. 1971 Sep;101(9):1165-7. Pubmed: 5096137
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. Pubmed: 9869358
Livesey G, Lund P: Binding of branched-chain 2-oxo acids to bovine serum albumin. Biochem J. 1982 Apr 15;204(1):265-72. Pubmed: 7115325
Schaefer K, von Herrath D, Erley CM, Asmus G: Calcium ketovaline as new therapy for uremic hyperphosphatemia. Miner Electrolyte Metab. 1990;16(6):362-4. Pubmed: 2089249
Schauder P, Schroder K, Langenbeck U: Serum branched-chain amino and keto acid response to a protein-rich meal in man. Ann Nutr Metab. 1984;28(6):350-6. Pubmed: 6393856
Shigematsu Y, Kikuchi K, Momoi T, Sudo M, Kikawa Y, Nosaka K, Kuriyama M, Haruki S, Sanada K, Hamano N, et al.: Organic acids and branched-chain amino acids in body fluids before and after multiple exchange transfusions in maple syrup urine disease. J Inherit Metab Dis. 1983;6(4):183-9. Pubmed: 6422161
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. Pubmed: 6581765
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Bouveault, L. etal., Bull. Soc. Chim. Fr., 1901, 1031; Singh, J. etal., Org. Prep. Proced. Int., 1989, 21, 501; Hata, H. etal., Synthesis, 1991, 289

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16530
HMDB ID	HMDB00019
Pubchem Compound ID	49
Kegg ID	C00141
ChemSpider ID	48
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	KIV

a-Ketoisovaleric acid (PAMDB000004)

Structure for a-Ketoisovaleric acid (PAMDB000004)