ContaminantDB: (R)-3-Hydroxyisobutyric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:32:08 UTC

Update Date

2016-11-09 01:17:30 UTC

Accession Number

CHEM022418

Identification

Common Name

(R)-3-Hydroxyisobutyric acid

Class

Small Molecule

Description

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) [HMDB]

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical 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 Mass

104.105 g/mol

Monoisotopic Mass

104.047 g/mol

CAS Registry Number

1910-47-0

IUPAC Name

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

Traditional Name

(R)-3-hydroxyisobutyric acid

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-00f48b549b40517fc756	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00gr-9720000000-2a61310303ff8f2a7b42	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9500000000-543c65dad21c233fc8a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052o-9000000000-7b7dcb34e28cb55ddafb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-27deee4c6a386a43ebc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-a7aa709e1985355b4bd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pi0-9200000000-01a40fbe4d19283ef080	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-622de763b5ea31ff4ee6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uki-9700000000-04713faa703ce789efb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9100000000-b0202d15bd6411bc7d80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-d2c32880fd340aac0bad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap3-9000000000-6c76b805d02ad21ab06a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aou-9000000000-fc5e7dbe1e224cc87d4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-021ab3207a43699617f4	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000336

FooDB ID

FDB021960

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

9392288

ChEBI ID

Not Available

PubChem Compound ID

11217234

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. 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.

2. Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105.

3. Gray RG, Pollitt RJ, Webley J: Methylmalonic semialdehyde dehydrogenase deficiency: demonstration of defective valine and beta-alanine metabolism and reduced malonic semialdehyde dehydrogenase activity in cultured fibroblasts. Biochem Med Metab Biol. 1987 Aug;38(1):121-4.

4. Roe CR, Struys E, Kok RM, Roe DS, Harris RA, Jakobs C: Methylmalonic semialdehyde dehydrogenase deficiency: psychomotor delay and methylmalonic aciduria without metabolic decompensation. Mol Genet Metab. 1998 Sep;65(1):35-43.

5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.

(R)-3-Hydroxyisobutyric acid (CHEM022418)

Structure for CHEM022418: (R)-3-Hydroxyisobutyric acid