ChemFOnt: Showing chemical card for 3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid (CFc000000309)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:40 UTC

Chemfont ID

CFc000000309

Molecule Identification

Common Name

3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid

Definition

3-Hydroxy-2-methyl-butanoic acid (HMBA) is a normal urinary metabolite involved in the isoleucine catabolism, as well as presumably b-oxidation of fatty acids and ketogenesis, excreted in abnormally high amounts in beta-ketothiolase deficiency. Differences in the enantiomeric ratio of HMBA may originate from the enantioselectivity of different enzyme systems (PMID 10755375 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-2-methyl-[S-(R,R)]-butanoate	Generator
3-Hydroxy-2-methyl-[S-(r,r)]-butanoate	HMDB
3-Hydroxy-2-methyl-[S-(r,r)]-butanoic acid	HMDB
[S-(R,R)]-3-Hydroxy-2-methyl-butanoate	HMDB
[S-(R,R)]-3-Hydroxy-2-methyl-butanoic acid	HMDB

Chemical Formula

C₅H₁₀O₃

Average Molecular Weight

118.1311

Monoisotopic Molecular Weight

118.062994186

IUPAC Name

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

Traditional Name

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

CAS Registry Number

84567-98-6

SMILES

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

InChI Identifier

InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4-/m1/s1

InChI Key

VEXDRERIMPLZLU-QWWZWVQMSA-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

Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Methyl-branched fatty acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000410)
Cell membrane (HMDB: HMDB0000410)

Organelle

Adiposome (HMDB: HMDB0000410)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000410)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000410)

Source

Endogenous

Endogenous (HMDB: HMDB0000410)

Animal

Animal (HMDB: HMDB0000410)

Exogenous

Food

Food (HMDB: HMDB0000410)

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: HMDB0000410)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000410)

Lipid metabolism pathway (HMDB: HMDB0000410)

Biochemical process

Lipid transport (HMDB: HMDB0000410)

Role

Biological role

Energy source (HMDB: HMDB0000410)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	336 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.16	ChemAxon
logS	0.45	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.04 m³·mol⁻¹	ChemAxon
Polarizability	11.8 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

External Links

HMDB ID

HMDB0000410

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022026

KNApSAcK ID

Not Available

Chemspider ID

13628080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5399

PubChem Compound

12313369

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kikukawa, Tadashi; Imaida, Motomasa; Tai, Akira. Synthesis of the sex-attractant of pine sawflies (diprion species); (2S,3R,7R)- and (2S,3R,7S)-3,7-dimethylpentadecan-2-ol. Chemistry Letters (1982), (11), 1799-802.

Showing chemical card for 3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid (CFc000000309)

MOL for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

3D MOL for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

3D SDF for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

3D-SDF for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

PDB for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

3D PDB for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

SMILES for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

INCHI for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

Structure for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)

3D Structure for CFc000000309 (3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid)