Bovine Metabolome Database: Showing metabocard for Gamma-Butyrolactone (BMDB0000549)

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 22:32:36 UTC

Update Date

2020-05-11 20:29:16 UTC

BMDB ID

BMDB0000549

Secondary Accession Numbers

BMDB00549

Metabolite Identification

Common Name

Gamma-Butyrolactone

Description

gamma-Butyrolactone, also known as 1,4-butanolide or 4-hydroxy-butanoate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, gamma-butyrolactone is considered to be a fatty ester. gamma-Butyrolactone exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on gamma-Butyrolactone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Butanolide	ChEBI
1,4-Butanolide	ChEBI
1,4-Lactone	ChEBI
4-Butyrolactone	ChEBI
4-Deoxytetronic acid	ChEBI
4-Hydroxybutyric acid lactone	ChEBI
Butyrolactone	ChEBI
Dihydro-2(3H)-furanone	ChEBI
gamma-Butanolactone	ChEBI
gamma-Hydroxybutyric acid lactone	ChEBI
gamma-Hydroxybutyrolactone	ChEBI
Tetrahydrofuran-2-one	ChEBI
4-Deoxytetronate	Generator
4-Hydroxybutyrate lactone	Generator
g-Butanolactone	Generator
Γ-butanolactone	Generator
g-Hydroxybutyrate lactone	Generator
g-Hydroxybutyric acid lactone	Generator
gamma-Hydroxybutyrate lactone	Generator
Γ-hydroxybutyrate lactone	Generator
Γ-hydroxybutyric acid lactone	Generator
g-Hydroxybutyrolactone	Generator
Γ-hydroxybutyrolactone	Generator
g-Butyrolactone	Generator
Γ-butyrolactone	Generator
1-Oxacyclopentan-2-one	HMDB
2,3,4,5-Tetrahydro-2-furanone	HMDB
2-Oxolanone	HMDB
2-Oxotetrahydrofuran	HMDB
4,5-Dihydro-2(3H)-furanone	HMDB
4-Butanolide	HMDB
4-Hydroxy-butanoate	HMDB
4-Hydroxy-butanoic acid	HMDB
4-Hydroxy-butanoic acid g-lactone	HMDB
4-Hydroxybutanoate	HMDB
4-Hydroxybutanoic acid	HMDB
4-Hydroxybutanoic acid lactone	HMDB
Butyric acid lactone	HMDB
g-Butalactone	HMDB
g-Butyryllactone	HMDB
gamma-Butalactone	HMDB
gamma-Butyryllactone	HMDB
GBL	HMDB
Paint clean g	HMDB
Tetrahydro-2-furanone	HMDB
4 Butyrolactone	HMDB
gamma Butyrolactone	HMDB
Furanone, tetrahydro 2	HMDB
1,4 Butanolide	HMDB
4 Hydroxybutyric acid lactone	HMDB
Lactone, 4-hydroxybutyric acid	HMDB
gamma-Butyrolactone	MeSH

Chemical Formula

C₄H₆O₂

Average Molecular Weight

86.0892

Monoisotopic Molecular Weight

86.036779436

IUPAC Name

oxolan-2-one

Traditional Name

butyrolactone

CAS Registry Number

96-48-0

SMILES

O=C1CCCO1

InChI Identifier

InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2

InChI Key

YEJRWHAVMIAJKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butan-4-olide (CHEBI:42639 )
Lactones (LMFA07040004 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-45 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000.0 mg/mL	Not Available
LogP	-0.64	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.11	ALOGPS
logP	0.15	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.31 m³·mol⁻¹	ChemAxon
Polarizability	8.23 Å³	ChemAxon
Number of Rings	1	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 - EI-B (Non-derivatized)	splash10-004l-9000000000-500445dc73cb69119e6b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-9000000000-d3df175d3315ed446e14	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9000000000-500445dc73cb69119e6b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-9000000000-d3df175d3315ed446e14	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-bd4b413f20907d13a107	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-4a6de93563809aa51a33	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-4a6de93563809aa51a33	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-b5163f6eb1e8004e61a9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-004l-9000000000-1066d349a6023c66dd64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-002f-9000000000-d3df175d3315ed446e14	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-fb7c9ada825a0c62979f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-9000000000-95fda8a898d02f7e71ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9000000000-c8282365f175b61ca8c0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-ec20127c74818b1f634d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9000000000-86d21b481322417edf81	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4f454124d6cece18a212	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-507998514018a44c4cf0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9000000000-d4ec4947321dfb11fab4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b2a1436205f5365513b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-709821dd006aa045c8b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-ffe2d9473d85a58305c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a4219a074939d10a0f5f	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-004l-9000000000-2fc3f4165b5808b41e93	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Neuron

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000549

DrugBank ID

DB04699

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gamma-Butyrolactone

METLIN ID

5533

PubChem Compound

7302

PDB ID

Not Available

ChEBI ID

42639

References

Synthesis Reference

Zhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang. Process for preparation of g-butyrolactone with high yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 13 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 Gamma-Butyrolactone (BMDB0000549)

Structure for BMDB0000549 (Gamma-Butyrolactone)

Enzymes