P. aeruginosa Metabolome Database: (R)-2,3-Dihydroxy-isovalerate (PAMDB000589)

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

PAMDB000589

Identification

Name:

(R)-2,3-Dihydroxy-isovalerate

Description:

(r)-2,3-dihydroxy-isovalerate belongs to the class of Branched Fatty Acids. These are fatty acids containing a branched chain. (inferred from compound structure)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α,β-dihydroxy-isovalerate
α,β-dihydroxy-isovaleric acid
(2R)-2,3-dihydroxy-3-methylbutanoate
(2R)-2,3-dihydroxy-3-methylbutanoic acid
(R)-2,3-dihydroxy-3-methylbutanoate
(R)-2,3-dihydroxy-3-methylbutanoic acid
(R)-2,3-Dihydroxy-isovaleric acid
2,3-dihydroxy-isovalerate
2,3-Dihydroxy-isovaleric acid

Chemical Formula:

C₅H₁₀O₄

Average Molecular Weight:

134.1305

Monoisotopic Molecular Weight:

134.057908808

InChI Key:

JTEYKUFKXGDTEU-VKHMYHEASA-N

InChI:

InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)/t3-/m0/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

(R)-2,3-dihydroxy-isovalerate

SMILES:

CC(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

2,3-dihydroxy-3-methylbutanoic acid (CHEBI:15684 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	529.0 mg/mL	ALOGPS
logP	-0.83	ALOGPS
logP	-0.82	ChemAxon
logS	0.6	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-3.2	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	2	ChemAxon
Refractivity	29.44 m³·mol^-1	ChemAxon
Polarizability	12.48 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:

Metabolic pathways pae01100
Pantothenate and CoA biosynthesis pae00770
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	splash10-00kr-4900000000-196ffbbf313a33f24f27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ri-9300000000-aebebbbe2c7c11465a67	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-92af6a04d8cb7601ab35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9500000000-2837622949a6bd688094	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00s9-9400000000-0fc7aa81197fc5feb444	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9000000000-45f3b95b2f30ea8445c1	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
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	15684
HMDB ID	HMDB12141
Pubchem Compound ID	440279
Kegg ID	C04272
ChemSpider ID	389255
Wikipedia ID	Not Available
BioCyc ID	DIOH-ISOVALERATE
EcoCyc ID	DIOH-ISOVALERATE

(R)-2,3-Dihydroxy-isovalerate (PAMDB000589)

Structure for (R)-2,3-Dihydroxy-isovalerate (PAMDB000589)