Livestock Metabolome Database: Showing metabocard for 4-Hydroxybutyric acid (LMDB00226)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:08 UTC

Update Date

2016-07-20 20:52:08 UTC

Lmdb

LMDB00226

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxybutyric acid

Description

4-Hydroxybutyric acid (GHB) is a precursor and a metabolite of gamma-aminobutyric acid (GABA), it is anticipated that GHB acts as a central nervous. system (CNS)neuromodulator, mediating its effects through GABA and GHB-specific receptors, or by affecting dopamine transmission.(PMID: 16620539 ). Gamma-hydroxybutyric acid (GHB) occurs naturally in all. mammals, but its function remains unknown. GHB is labeled as an illegal drug in most countries,but also used as a legal drug (Xyrem) in patients with narcolepsy. In high doses, GHB inhibits the CNS, inducing sleep and inhibiting the respiratory drive. In lower doses, its euphoriant effect predominates (PMID: 17658710 ).

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 and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	206 +/- 82 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	206 +/- 82 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	217 +/- 22 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	239 +/- 48 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	253 +/- 94 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	206.2 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	216.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	239.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	253.1 uM	Not Available	Bovine	22959937	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000710

FooDB ID

FDB022196

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

4-HYDROXY-BUTYRATE

METLIN ID

5678

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB21338

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

LeBeau MA, Montgomery MA, Morris-Kukoski C, Schaff JE, Deakin A, Levine B: A comprehensive study on the variations in urinary concentrations of endogenous gamma-hydroxybutyrate (GHB). J Anal Toxicol. 2006 Mar;30(2):98-105. [16620539 ]
Kankaanpaa A, Liukkonen R, Ariniemi K: Determination of gamma-hydroxybutyrate (GHB) and its precursors in blood and urine samples: a salting-out approach. Forensic Sci Int. 2007 Aug 6;170(2-3):133-8. Epub 2007 Jul 20. [17658710 ]

Showing metabocard for 4-Hydroxybutyric acid (LMDB00226)

Structure for LMDB00226 (4-Hydroxybutyric acid)