Bovine Metabolome Database: Showing metabocard for 4-Hydroxybutyric acid (BMDB0000710)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:17 UTC

Update Date

2020-06-04 20:23:42 UTC

BMDB ID

BMDB0000710

Secondary Accession Numbers

BMDB00710

Metabolite Identification

Common Name

4-Hydroxybutyric acid

Description

4-Hydroxybutyric acid, also known as 4-hydroxybutanoate or gamma hydroxybutyrate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 4-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxybutyric acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Carboxypropoxy acid	ChEBI
4-Hydroxy-butyric acid	ChEBI
4-Hydroxyalkanoic acid	ChEBI
4-Hydroxybutanoate	ChEBI
4-Hydroxybutanoic acid	ChEBI
4-Hydroxycarboxylic acid	ChEBI
Gamma Hydroxybutyric acid	ChEBI
gamma-Hydroxybutyric acid	ChEBI
GHB	ChEBI
Oxy-N-butyric acid	ChEBI
Xyrem	ChEBI
4-Hydroxy-butyrate	Generator
4-Hydroxyalkanoate	Generator
4-Hydroxycarboxylate	Generator
g Hydroxybutyrate	Generator
g Hydroxybutyric acid	Generator
gamma Hydroxybutyrate	Generator
Γ hydroxybutyrate	Generator
Γ hydroxybutyric acid	Generator
g-Hydroxybutyrate	Generator
g-Hydroxybutyric acid	Generator
gamma-Hydroxybutyrate	Generator
Γ-hydroxybutyrate	Generator
Γ-hydroxybutyric acid	Generator
Oxy-N-butyrate	Generator
4-Hydroxybutyrate	Generator
4-Hydroxy-butanoate	HMDB
4-Hydroxy-butanoic acid	HMDB
4-Hydroxybutyrate sodium	HMDB
4-Hydroxybutyric acid monosodium salt	HMDB
gamma-Hydroxy butyrate	HMDB
gamma-Hydroxy sodium butyrate	HMDB
gamma-Hydroxybutyrate sodium	HMDB
Hydroxybutyric acid	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

4-hydroxybutanoic acid

Traditional Name

gamma hydroxybutyric acid

CAS Registry Number

591-81-1

SMILES

OCCCC(O)=O

InChI Identifier

InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)

InChI Key

SJZRECIVHVDYJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Short-chain hydroxy acid
Hydroxy fatty acid
Straight chain fatty 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

4-hydroxy monocarboxylic acid (CHEBI:30830 )
hydroxybutyric acid (CHEBI:30830 )
Hydroxy fatty acids (LMFA01050006 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.63	ALOGPS
logP	-0.51	ChemAxon
logS	0.68	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-2.4	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	3	ChemAxon
Refractivity	23.8 m³·mol⁻¹	ChemAxon
Polarizability	10.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0159-2920000000-131f94186a93d0aa315d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2920000000-131f94186a93d0aa315d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-7240955b6b16291cf793	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-9000000000-915d32c0dbd6e6d19a55	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9610000000-52e5254f6eba257ad184	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-14ii-9400000000-77378d9d837f1823ed37	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0udi-0900000000-ca02549abb7c7402b481	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-0900000000-942af3cd327a2dd39887	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-671c45f3bda2eabba3c1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-36fabc35679210a4621a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-2900000000-146b4ca6698f6c40d476	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-4900000000-32e86ae76401d830a8a1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-8900000000-07fc17585cf5e8d2ba9b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0pbi-9400000000-70777a3c6521e72b59b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0a4i-9000000000-cad0cc415c906a783cfc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0zg0-9500000000-9dfcd62aeff3ff1e731d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0pb9-9300000000-0e1b3056ef85c0fbe59d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-9200000000-144d4f05dfc0b2dbd827	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a4i-9100000000-5a807248d180fcc738ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9000000000-aeb70e18a8467ef1b4b1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9000000000-50691ede3dffed6a4afb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0a4i-9000000000-13adfaf490932a7c0fb9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-000i-9000000000-3051dc4fe82b4abf5478	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0002-0900000000-8f691ae372d6f1d18226	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9100000000-80636ab7e3cb47d4d58f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n4-9000000000-71899633e269029ab7f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-910235f5bc92bcca7469	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-8900000000-5890f0a527dd16d9ac75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0k9i-9200000000-241210fedf9304168090	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-21d09118dfcfcb093f8d	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-d55d971a361b41564681	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm

Biospecimen Locations

Liver
Mammary Gland
Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000710

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022196

KNApSAcK ID

Not Available

Chemspider ID

9984

KEGG Compound ID

C01991

BioCyc ID

4-HYDROXY-BUTYRATE

BiGG ID

Not Available

Wikipedia Link

Oxybate

METLIN ID

5678

PubChem Compound

10413

PDB ID

Not Available

ChEBI ID

30830

References

Synthesis Reference

Takigawa, Shinichiro; Araya, Shuzo. Process for the preparation of g-hydroxybutyric acid as a synthetic intermediate. Jpn. Kokai Tokkyo Koho (1988), 3 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Hydroxyacid-oxoacid transhydrogenase, mitochondrial

General function:: Energy production and conversion
Specific function:: Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). L-3-hydroxybutyrate (L-3-OHB) is also a substrate for HOT when using 2-KG as hydrogen acceptor, resulting in the formation of D-2-HG (By similarity).
Gene Name:: ADHFE1
Uniprot ID:: A6QP15
Molecular weight:: 50343.0

Showing metabocard for 4-Hydroxybutyric acid (BMDB0000710)

Structure for BMDB0000710 (4-Hydroxybutyric acid)

Enzymes