P. aeruginosa Metabolome Database: (R) 2,3-Dihydroxy-3-methylvalerate (PAMDB000822)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000822

Identification

Name:

(R) 2,3-Dihydroxy-3-methylvalerate

Description:

(R) 2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, that generates not only isoleucine and valine, but also leucine. (R) 2,3-Dihydroxy-methylvalerate is generated from 3-Hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC:4.2.1.9).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2R,3R)-2,3-dihydroxy-3-methylpentanoate
(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid
(R) 2,3-Dihydroxy-3-methylvaleric acid
(R)-2,3-Dihydroxy-3-methylpentanoate
(R)-2,3-Dihydroxy-3-methylpentanoic acid
(R)-2,3-Dihydroxy-3-methylvalerate
(R)-2,3-Dihydroxy-3-methylvaleric acid
1-Keto-2-methylvalerate
1-Keto-2-methylvaleric acid
2,3-Dihydroxy-3-Methyl-Valerate
2,3-Dihydroxy-3-Methyl-Valeric acid
2,3-Dihydroxy-3-methylpentanoate
2,3-Dihydroxy-3-methylpentanoic acid
2,3-Dihydroxy-Valerianate
2,3-Dihydroxy-Valerianic Acid
4,5-Dideoxy-3-C-methyl-pentonate
4,5-Dideoxy-3-C-methyl-pentonic acid
a,b-Dihydroxy-b-methylvalerate
a,b-Dihydroxy-b-methylvaleric acid
Alpha,beta-Dihydroxy-beta-methylvalerate
Alpha,beta-Dihydroxy-beta-methylvaleric acid
CID8
DMV
α,β-Dihydroxy-β-methylvalerate
α,β-Dihydroxy-β-methylvaleric acid

Chemical Formula:

C₆H₁₂O₄

Average Molecular Weight:

148.1571

Monoisotopic Molecular Weight:

148.073558872

InChI Key:

PDGXJDXVGMHUIR-UJURSFKZSA-N

InChI:

InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1

CAS number:

562-43-6

IUPAC Name:

(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid

Traditional IUPAC Name:

(2R,3R)-2,3-dihydroxy-3-methylpentanoic acid

SMILES:

CC[C@@](C)(O)[C@@H](O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Hydroxy fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Branched fatty acid
Beta-hydroxy acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dihydroxy monocarboxylic acid (CHEBI:27512 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	486.0 mg/mL	ALOGPS
logP	-0.44	ALOGPS
logP	-0.3	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.96 m³·mol^-1	ChemAxon
Polarizability	14.43 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:

(R) 2,3-Dihydroxy-3-methylvalerate > 3-Methyl-2-oxovaleric acid + Water
2-Aceto-2-hydroxy-butyrate + Hydrogen ion + NADPH <> (R) 2,3-Dihydroxy-3-methylvalerate + NADP
(R) 2,3-Dihydroxy-3-methylvalerate + NADP <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate + NADPH + Hydrogen ion
(R) 2,3-Dihydroxy-3-methylvalerate + NADP > 2-Aceto-2-hydroxy-butyrate + NADPH
(R)-2,3-Dihydroxy-isovalerate + Hydrogen ion + NADPH + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
2-Aceto-2-hydroxy-butyrate + NADPH + Hydrogen ion + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
(R) 2,3-Dihydroxy-3-methylvalerate > Water + 3-Methyl-2-oxovaleric acid + 3-Methyl-2-oxovaleric acid

Pathways:

Valine, leucine and isoleucine biosynthesis pae00290

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05aj-7900000000-ed4255c918254a1dc462	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kar-9600000000-420faa83ea76001db2e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9000000000-393b15b5811231e32693	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-2900000000-d582074beb8b89338fa5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9400000000-5ee3e425ebda8358d337	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05g0-9000000000-db72ead6bd87a129b325	View in MoNA

References

References:

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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	27512
HMDB ID	HMDB12140
Pubchem Compound ID	448154
Kegg ID	C06007
ChemSpider ID	395044
Wikipedia ID	Not Available
BioCyc ID	1-KETO-2-METHYLVALERATE
EcoCyc ID	1-KETO-2-METHYLVALERATE
Ligand Expo	DMV

(R) 2,3-Dihydroxy-3-methylvalerate (PAMDB000822)

Structure for (R) 2,3-Dihydroxy-3-methylvalerate (PAMDB000822)