Showing Compound 2-Hydroxybutyric acid (FDB021867)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:13 UTC

Update date

2019-11-26 03:21:00 UTC

Primary ID

FDB021867

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Hydroxybutyric acid

Description

2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632) [HMDB]

CAS Number

600-15-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+/-)a-hydoxy butyrate	HMDB
(+/-)a-hydoxy butyric acid	HMDB
(+/-)alpha-hydoxy butyrate	HMDB
(+/-)α-hydoxy butyrate	HMDB
(+/-)α-hydoxy butyric acid	HMDB
(RS)-2-Hydroxybutyrate	HMDB
(RS)-2-Hydroxybutyric acid	HMDB
2-Hydroxy-butanoate	HMDB
2-hydroxy-Butanoate	hmdb
2-Hydroxy-butanoic acid	HMDB

Showing 1 to 10 of 57 entries

Predicted Properties

Property	Value	Source
Water Solubility	484 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	0.051	ChemAxon
logS	0.67	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-3.8	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	23.36 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

2-hydroxybutanoic acid

InChI Identifier

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

InChI Key

AFENDNXGAFYKQO-UHFFFAOYSA-N

Isomeric SMILES

CCC(O)C(O)=O

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

Classification

Description

Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxybutyric acid (CHEBI:1148 )
2-hydroxy monocarboxylic acid (CHEBI:1148 )
Hydroxy fatty acids (LMFA01050004 )

Ontology

Endogenous

Biological location:

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Metabolite

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	2-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-001j-0900000000-44dd1bf8072e5731bac4	Spectrum
GC-MS	2-Hydroxybutyric acid, 2 TMS, GC-MS Spectrum	splash10-00e9-9700000000-93eba027d5343e3d6ce1	Spectrum
GC-MS	2-Hydroxybutyric acid, 2 TMS, GC-MS Spectrum	splash10-001i-1910000000-3bc9898b26df33cad244	Spectrum
GC-MS	2-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-9000000000-4d935da8e593ec61fd96	Spectrum
GC-MS	2-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-001j-0900000000-44dd1bf8072e5731bac4	Spectrum
GC-MS	2-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-00e9-9700000000-93eba027d5343e3d6ce1	Spectrum
GC-MS	2-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-001i-1910000000-3bc9898b26df33cad244	Spectrum
Predicted GC-MS	2-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6u-9000000000-0d95c1179b1b00650601	Spectrum
Predicted GC-MS	2-Hydroxybutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00v0-9520000000-598a2bd61c303327bd8f	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4j-9200000000-e3b371c29b9ebed3199b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9700000000-bccfada2c97e04d34417	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-9000000000-4d935da8e593ec61fd96	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-2900000000-3c7915ea71886873f024	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0zfr-7900000000-d91c840306a06d4ea513	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9500000000-8f04a5941997004743d2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-cef703dc6f30af7834a8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-1e7e6e8a895c4c1d51db	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-4900000000-d0907a0b08e0d829ceca	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-d826b54f814ac185b4db	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-3727124ed618f038b514	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum