3-Hydroxybutyric acid (YMDB01561)

Identification

YMDB ID

YMDB01561

Name

3-Hydroxybutyric acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

3-Hydroxybutyric acid, also known as 3-hydroxybutyrate or 3-hydroxybuttersaeure, 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. 3-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 3-Hydroxybutyric acid is a potentially toxic compound.

Structure

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

Synonyms

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

CAS number

300-85-6

Weight

Average: 104.1045
Monoisotopic: 104.047344122

InChI Key

WHBMMWSBFZVSSR-UHFFFAOYSA-N

InChI

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

IUPAC Name

3-hydroxybutanoic acid

Traditional IUPAC Name

3 hydroxybutyrate

Chemical Formula

C₄H₈O₃

SMILES

CC(O)CC(O)=O

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

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 )

Physical Properties

State

Solid

Charge

Melting point

46 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Fatty acid biosynthesis

PW002458

KEGG Pathways

Fatty acid biosynthesis

ec00061

SMPDB Reactions

Acetoacetic acid → 3-Hydroxybutyric acid

3-Hydroxybutyric acid → But-2-enoic acid

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
600 ± 30 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0900000000-92be5c49a099fe1d9865	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-01ot-1920000000-c93138bf9d35643fef30	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-8900000000-e632e14fb4be28bdb786	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014l-1900000000-e192caba63f034040624	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-92be5c49a099fe1d9865	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ot-1920000000-c93138bf9d35643fef30	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-8900000000-e632e14fb4be28bdb786	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014l-1900000000-e192caba63f034040624	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d06c5ac1a3733a38ea05	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9000000000-63f261a4dc876e264246	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01ei-9710000000-2652bd46b41e50defdb0	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-9200000000-4156904e7472b5e97249	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9300000000-505ae46abb0c49c78b1e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfr-9600000000-dfed69c37c1a4d794440	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0zfr-4900000000-537084557f5986f16b31	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-4900000000-537084557f5986f16b31	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-9000000000-7f0ec480b3c3c3911acd	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-9100000000-05c4623b015ff4300a6d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-9000000000-cbe0653845ffe4dc6ad4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e55d47308c7464e4cb22	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-06dfbf939f6d19983ebe	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-48b6e9b8656d41bff9cf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-f7d61596ff4428fe6b09	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0007-9000000000-7fc414806153ebd8822c	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	20067
HMDB ID	HMDB00357
Pubchem Compound ID	441
Kegg ID	C01089
ChemSpider ID	428
FOODB ID	FDB021797
Wikipedia ID	3-hydroxybutyrate
BioCyc ID	CPD-335

Structure for #<Compound:0xa9d73eb8>