Showing Compound (S)-3-Hydroxyisobutyric acid (FDB021877)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:23 UTC

Update date

2020-09-17 15:40:45 UTC

Primary ID

FDB021877

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-3-Hydroxyisobutyric acid

Description

(S)-3-Hydroxyisobutyric acid, also known as (S)-3-hydroxy-2-methylpropanoate or 3-hydroxy-isobutyrate, 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 (S)-3-Hydroxyisobutyric acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-3-Hydroxyisobutyric acid exists in all living species, ranging from bacteria to humans. The severity of this disease varies from case to case (S)-3-hydroxyisobutyric acid can be converted into (S)-methylmalonic acid semialdehyde through its interaction with the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In humans, (S)-3-hydroxyisobutyric acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway (S)-3-Hydroxyisobutyric acid is an intermediate in the metabolic pathways of L-valine and L-thymine amino acids. The deficient enzyme in 3HiB-uria remains unclear (S)-3-Hydroxyisobutyric acid is a potentially toxic compound (S)-3-Hydroxyisobutyric acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, colorectal cancer, and diabetes mellitus type 2; (S)-3-hydroxyisobutyric acid has also been linked to the inborn metabolic disorder 3-hydroxyisobutyric aciduria.

CAS Number

2068-83-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(S)-3-Hydroxy-2-methylpropanoic acid	ChEBI
(S)-3-Hydroxy-2-methylpropionic acid	ChEBI
(S)-3-Hydroxy-2-methylpropanoate	Generator
(S)-3-Hydroxy-2-methylpropionate	Generator
(S)-3-Hydroxyisobutyrate	Generator
2-Methyl-L-(+)-hydracrylate	HMDB
2-Methyl-L-(+)-hydracrylic acid	HMDB
3-Hydroxy(iso)butyric acid	HMDB
3-Hydroxy-2-methyl-(S)-propanoate	HMDB
3-Hydroxy-2-methyl-(S)-propanoic acid	HMDB
3-Hydroxy-2-methylpropanoate	HMDB
3-Hydroxy-2-methylpropanoic acid	HMDB
3-Hydroxy-isobutyrate	HMDB
3-Hydroxyisobutyrate	HMDB
3-Hydroxyisobutyric acid	HMDB
(2S)-3-Hydroxy-2-methylpropanoic acid	HMDB
(2S)-3-Hydroxy-2-methylpropionic acid	HMDB
(S)-beta-Hydroxyisobutyric acid	HMDB
(S)-Β-hydroxyisobutyric 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-methylpropionic acid	HMDB
DL-3-Hydroxyisobutyric acid	HMDB
L-(+)-beta-Hydroxyisobutyric acid	HMDB
L-(+)-Β-hydroxyisobutyric acid	HMDB
beta-Hydroxyisobutyric acid	HMDB
Β-hydroxyisobutyric acid	HMDB
3-Hydroxy-2-isobutyrate	HMDB
3-Hydroxy-2-isobutyric acid	HMDB
(S)-3-Hydroxyisobutyric acid	HMDB
2-methyl-L-(+)-Hydracrylate	hmdb
2-methyl-L-(+)-Hydracrylic acid	hmdb
3-hydroxy-2-methyl-(S)-Propanoate	hmdb
3-hydroxy-2-methyl-(S)-Propanoic acid	hmdb
3-hydroxy-isobutyrate	hmdb

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

Chemical Formula

C4H8O3

IUPAC name

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

InChI Identifier

InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

InChI Key

DBXBTMSZEOQQDU-VKHMYHEASA-N

Isomeric SMILES

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

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

Classification

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

3-hydroxyisobutyric acid (CHEBI:37373 )

Ontology

Physiological effect

Health effect:

Health condition:

Diabetes mellitus type 2

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9000000000-dd1c22f7a337d3289497	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gr-9720000000-2a61310303ff8f2a7b42	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-8900000000-b51c12e744025b833f31	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9100000000-0d72fcffff267d7bc980	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9500000000-543c65dad21c233fc8a8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052o-9000000000-7b7dcb34e28cb55ddafb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-27deee4c6a386a43ebc3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-a7aa709e1985355b4bd9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pi0-9200000000-01a40fbe4d19283ef080	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-622de763b5ea31ff4ee6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap3-9000000000-6c76b805d02ad21ab06a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aou-9000000000-fc5e7dbe1e224cc87d4f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-021ab3207a43699617f4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uki-9700000000-04713faa703ce789efb3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9100000000-b0202d15bd6411bc7d80	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-d2c32880fd340aac0bad	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum