ChemFOnt: Showing chemical card for (R)-3-Hydroxyisobutyric acid (CFc000000238)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:35 UTC

Chemfont ID

CFc000000238

Molecule Identification

Common Name

(R)-3-Hydroxyisobutyric acid

Definition

(R)-3-Hydroxyisobutyric acid (3-HIBA) is an organic acid. The chiral metabolites 3-hydroxyisobutyric acid (HIBA) and 3-aminoisobutyric acid (AIBA) are intermediates in the pathways of L-valine and thymine and play an important role in the diagnosis of the very rare inherited metabolic diseases 3-hydroxyisobutyric aciduria (OMIM: 236795 ) and methylmalonic semialdehyde dehydrogenase deficiency (OMIM: 603178 ) (PMID: 10686279 ). (R)-3-Hydroxyisobutyric acid has been identified in the human placenta (PMID: 32033212 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-3-Hydroxyisobutyrate	Generator
(R)-3-Hydroxy-2-methylpropionate	HMDB
(R)-3-Hydroxy-2-methylpropionic acid	HMDB
2-Methyl-(R)-hydracrylate	HMDB
2-Methyl-(R)-hydracrylic acid	HMDB
3-Hydroxy-2-methylpropionate	HMDB
D-(-)-3-Hydroxyisobutyrate	HMDB
D-(-)-3-Hydroxyisobutyric acid	HMDB
D-b-Hydroxyisobutyrate	HMDB
D-b-Hydroxyisobutyric acid	HMDB
delta-(-)-3-Hydroxyisobutyrate	HMDB
delta-(-)-3-Hydroxyisobutyric acid	HMDB
delta-beta-Hydroxyisobutyrate	HMDB
delta-beta-Hydroxyisobutyric acid	HMDB
R-b-Hydroxyisobutyrate	HMDB
R-b-Hydroxyisobutyric acid	HMDB
R-beta-Hydroxyisobutyrate	HMDB
R-beta-Hydroxyisobutyric acid	HMDB
3R-Hydroxy-isobutyrate	HMDB
(2R)-3-Hydroxy-2-methylpropanoic acid	HMDB
(2R)-3-Hydroxy-2-methylpropionic acid	HMDB
(R)-3-Hydroxy-2-methyl-propanoic acid	HMDB
(R)-3-Hydroxy-2-methyl-propionic acid	HMDB
(R)-3-Hydroxy-2-methylpropanoic acid	HMDB
(±)-3-hydroxy-2-methylpropanoic acid	HMDB
(±)-3-hydroxy-2-methylpropionic acid	HMDB
2-(Hydroxymethyl)propanoic acid	HMDB
2-(Hydroxymethyl)propionic acid	HMDB
2-Methyl-3-hydroxypropanoic acid	HMDB
2-Methyl-3-hydroxypropionic acid	HMDB
3-HIBA	HMDB
3-Hydroxy-2-methylpropanoic acid	HMDB
3-Hydroxy-2-methylpropionic acid	HMDB
3-Hydroxyisobutyric acid	HMDB
D-beta-Hydroxyisobutyric acid	HMDB
D-Β-hydroxyisobutyric acid	HMDB
DL-3-Hydroxyisobutyric acid	HMDB
R-3-Hydroxyisobutyric acid	HMDB
R-Β-hydroxyisobutyric acid	HMDB
beta-Hydroxyisobutyric acid	HMDB
Β-hydroxyisobutyric acid	HMDB
3-Hydroxy-2-isobutyrate	HMDB
3-Hydroxy-2-isobutyric acid	HMDB
(R)-3-Hydroxyisobutyric acid	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

(2R)-3-hydroxy-2-methylpropanoic acid

Traditional Name

(R)-3-hydroxyisobutyric acid

CAS Registry Number

1910-47-0

SMILES

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

InChI Identifier

InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

InChI Key

DBXBTMSZEOQQDU-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy fatty acids (LMFA01050382 )

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Diabetes mellitus type 2 (HMDB: HMDB0000336)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2614280)
Cerebrospinal Fluid (CSF) (PMID: 18502700)
Cerebrospinal fluid (HMDB: HMDB0000336)

Organ

Placenta (HMDB: HMDB0000336)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Source

Endogenous

Endogenous (HMDB: HMDB0000336)

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

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00000146)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	571 g/L	ALOGPS
logP	-0.47	ALOGPS
logP	-0.26	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Acidic)	4.37	ChemAxon
pKa (Strongest Basic)	-2.7	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	23.62 m³·mol⁻¹	ChemAxon
Polarizability	9.98 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

HMDB0000336

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021960

KNApSAcK ID

Not Available

Chemspider ID

9392288

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11217234

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Sprecher, M.; Sprinson, David B. Preparation of (R)-b-hydroxyisobutyric acid from threo-3-methyl-L-aspartate. Journal of Biological Chemistry (1966), 241(4), 868-71.

Showing chemical card for (R)-3-Hydroxyisobutyric acid (CFc000000238)

MOL for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

3D MOL for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

3D SDF for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

3D-SDF for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

PDB for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

3D PDB for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

SMILES for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

INCHI for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

Structure for CFc000000238 ((R)-3-Hydroxyisobutyric acid)

3D Structure for CFc000000238 ((R)-3-Hydroxyisobutyric acid)