ChemFOnt: Showing chemical card for (R)-2,3-Dihydroxy-isovalerate (CFc000007697)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:09 UTC

Chemfont ID

CFc000007697

Molecule Identification

Common Name

(R)-2,3-Dihydroxy-isovalerate

Definition

(R) 2,3-Dihydroxy-isovalerate 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-isovalerate is generated from 3-Hydroxy-3-methyl-2-oxobutanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) then it is converted to 2-Oxoisovalerate via the dihydroxy-acid dehydratase (EC:4.2.1.9).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2,3-Dihydroxy-isovaleric acid	ChEBI
(2R)-2,3-Dihydroxy-3-methylbutanoate	Kegg
(2R)-2,3-Dihydroxy-3-methylbutanoic acid	Generator
(R)-2,3-Dihydroxy-3-methylbutanoate	HMDB
(R)-2,3-Dihydroxy-3-methylbutanoic acid	HMDB
(R)-(-)-alpha,beta-Dihydroxyisovaleric acid	HMDB
(R)-(-)-α,β-Dihydroxyisovaleric acid	HMDB
(R)-2,3-Dihydroxy-isovalerate	HMDB

Chemical Formula

C₅H₁₀O₄

Average Molecular Weight

134.1305

Monoisotopic Molecular Weight

134.057908808

IUPAC Name

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

Traditional Name

(R)-2,3-dihydroxy-isovalerate

CAS Registry Number

19451-56-0

SMILES

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

InChI Identifier

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

InChI Key

JTEYKUFKXGDTEU-VKHMYHEASA-N

Chemical Taxonomy

Description

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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

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

Functional Ontology

Physiological effect

Health effect

Observation

Attachment loss (HMDB: HMDB0012141)
Missing teeth (HMDB: HMDB0012141)

Intervention

Periodontal Probing Depth (HMDB: HMDB0012141)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Urine (PMID: 26163321)
Feces (PMID: 28923537)

Cellular substructure

Cytoplasm (HMDB: HMDB0012141)
Cell membrane (HMDB: HMDB0012141)

Organelle

Adiposome (HMDB: HMDB0012141)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012141)

Source

Endogenous

Endogenous (HMDB: HMDB0012141)

Animal

Animal (HMDB: HMDB0012141)

Exogenous

Food

Food (HMDB: HMDB0012141)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012141)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012141)
Valine Biosynthesis (PathBank: SMP0002373)
Valine Biosynthesis (PathBank: SMP0121288)

Lipid metabolism pathway (HMDB: HMDB0012141)

Biochemical process

Lipid transport (HMDB: HMDB0012141)

Role

Biological role

Energy source (HMDB: HMDB0012141)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	529 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon