Showing Compound 3-Hydroxybutanoic acid (FDB021797)

Record Information

Version

1.0

Creation date

2011-04-08 19:48:08 UTC

Update date

2019-11-26 03:20:53 UTC

Primary ID

FDB021797

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Hydroxybutanoic acid

Description

3-Hydroxybutanoic acid is a ketone body. It is a chiral compound having two enantiomers. The concentration of beta-hydroxybutyrate, like that of other ketone bodies, is increased in ketosis. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA in a reaction catalyzed by the enzyme beta-hydroxybutyrate dehydrogenase and can be used as an energy source by the brain when blood glucose is low. Diabetic patients can have their ketone levels tested via urine or blood to indicate diabetic ketoacidosis. In alcoholic ketoacidosis, this ketone body is produced in greatest concentration. Both types of ketoacidosis result in an increasebeta-hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle stalling and shifting of glucose towards ketone body production. [Wikipedia]

CAS Number

300-85-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(1)-3-Hydroxybutyric acid	ChEBI
3 HBA	ChEBI
3-Hydroxybuttersaeure	ChEBI
3-OH-Butyric acid	ChEBI
beta-Hydroxy-N-butyric acid	ChEBI
beta-Hydroxybutanoic acid	ChEBI
beta-Hydroxybuttersaeure	ChEBI
beta-Hydroxybutyric acid	ChEBI
BHBA	ChEBI
DL-beta-Hydroxybutyric acid	ChEBI
(1)-3-Hydroxybutyrate	Generator
3-OH-Butyrate	Generator
b-Hydroxy-N-butyrate	Generator
b-Hydroxy-N-butyric acid	Generator
beta-Hydroxy-N-butyrate	Generator
Β-hydroxy-N-butyrate	Generator
Β-hydroxy-N-butyric acid	Generator
b-Hydroxybutanoate	Generator
b-Hydroxybutanoic acid	Generator
beta-Hydroxybutanoate	Generator
Β-hydroxybutanoate	Generator
Β-hydroxybutanoic acid	Generator
b-Hydroxybuttersaeure	Generator
Β-hydroxybuttersaeure	Generator
b-Hydroxybutyrate	Generator
b-Hydroxybutyric acid	Generator
beta-Hydroxybutyrate	Generator
Β-hydroxybutyrate	Generator
Β-hydroxybutyric acid	Generator
DL-b-Hydroxybutyrate	Generator
DL-b-Hydroxybutyric acid	Generator
DL-beta-Hydroxybutyrate	Generator
DL-Β-hydroxybutyrate	Generator
DL-Β-hydroxybutyric acid	Generator
3-Hydroxybutyrate	Generator
3-Hydroxy-butanoate	HMDB
3-Hydroxy-butanoic acid	HMDB
3-Hydroxy-butyrate	HMDB
3-Hydroxy-butyric acid	HMDB
3-Hydroxybutanoate	HMDB
3-Hydroxybutanoic acid	HMDB
Biopol	HMDB
DL-3-Hydroxybutyrate	HMDB
DL-3-Hydroxybutyric acid	HMDB
beta Hydroxybutyric acid	HMDB
3 Hydroxybutyric acid	HMDB
beta Hydroxybutyrate	HMDB
(+ -)-3-Hydroxybutyric acid	HMDB
3 Hydroxybutyrate	HMDB
3-Hydroxybutyric acid	manual
DL-β-hydroxybutyrate	Generator
DL-β-hydroxybutyric acid	Generator
β-hydroxy-N-butyrate	Generator
β-hydroxy-N-butyric acid	Generator
β-hydroxybutanoate	Generator
β-hydroxybutanoic acid	Generator
β-hydroxybuttersaeure	Generator
β-hydroxybutyrate	Generator
β-hydroxybutyric acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	539 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	-0.39	ChemAxon
logS	0.71	ALOGPS
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	-2.6	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	23.46 m³·mol⁻¹	ChemAxon
Polarizability	10.01 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

3-hydroxybutanoic acid

InChI Identifier

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

InChI Key

WHBMMWSBFZVSSR-UHFFFAOYSA-N

Isomeric SMILES

CC(O)CC(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

Short-chain hydroxy acid
Beta-hydroxy acid
Fatty 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

3-hydroxy monocarboxylic acid (CHEBI:20067 )
hydroxybutyric acid (CHEBI:20067 )
(omega-1)-hydroxy fatty acid (CHEBI:20067 )
Hydroxy fatty acids (LMFA01050005 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Obesity

Disposition

Source:

Endogenous

Biological:

Microbe:

Alcaligenes:

Alcaligenes eutrophus

Biological location:

Cell and elements:

Cell:

Nerve cell

Biofluid and excreta:

Organ and components:

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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0007-9000000000-7fc414806153ebd8822c	2014-09-20	View Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-92be5c49a099fe1d9865	Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-01ot-1920000000-c93138bf9d35643fef30	Spectrum
GC-MS	3-Hydroxybutanoic acid, 2 TMS, GC-MS Spectrum	splash10-00dj-8900000000-e632e14fb4be28bdb786	Spectrum
GC-MS	3-Hydroxybutanoic acid, 2 TMS, GC-MS Spectrum	splash10-014l-1900000000-e192caba63f034040624	Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-92be5c49a099fe1d9865	Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-01ot-1920000000-c93138bf9d35643fef30	Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-00dj-8900000000-e632e14fb4be28bdb786	Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-014l-1900000000-e192caba63f034040624	Spectrum
GC-MS	3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0900000000-d06c5ac1a3733a38ea05	Spectrum
Predicted GC-MS	3-Hydroxybutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-9000000000-63f261a4dc876e264246	Spectrum
Predicted GC-MS	3-Hydroxybutanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ei-9710000000-2652bd46b41e50defdb0	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-9200000000-4156904e7472b5e97249	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9300000000-505ae46abb0c49c78b1e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfr-9600000000-dfed69c37c1a4d794440	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0zfr-4900000000-537084557f5986f16b31	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-4900000000-537084557f5986f16b31	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-9000000000-7f0ec480b3c3c3911acd	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-9100000000-05c4623b015ff4300a6d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-9000000000-cbe0653845ffe4dc6ad4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e55d47308c7464e4cb22	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-06dfbf939f6d19983ebe	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-48b6e9b8656d41bff9cf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-f7d61596ff4428fe6b09	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum