Showing metabocard for Gamma-Butyrolactone (BMDB0000549)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:32:36 UTC
Update Date2020-05-11 20:29:16 UTC
BMDB IDBMDB0000549
Secondary Accession Numbers
  • BMDB00549
Metabolite Identification
Common NameGamma-Butyrolactone
Descriptiongamma-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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-ButanolideChEBI
1,4-ButanolideChEBI
1,4-LactoneChEBI
4-ButyrolactoneChEBI
4-Deoxytetronic acidChEBI
4-Hydroxybutyric acid lactoneChEBI
ButyrolactoneChEBI
Dihydro-2(3H)-furanoneChEBI
gamma-ButanolactoneChEBI
gamma-Hydroxybutyric acid lactoneChEBI
gamma-HydroxybutyrolactoneChEBI
Tetrahydrofuran-2-oneChEBI
4-DeoxytetronateGenerator
4-Hydroxybutyrate lactoneGenerator
g-ButanolactoneGenerator
Γ-butanolactoneGenerator
g-Hydroxybutyrate lactoneGenerator
g-Hydroxybutyric acid lactoneGenerator
gamma-Hydroxybutyrate lactoneGenerator
Γ-hydroxybutyrate lactoneGenerator
Γ-hydroxybutyric acid lactoneGenerator
g-HydroxybutyrolactoneGenerator
Γ-hydroxybutyrolactoneGenerator
g-ButyrolactoneGenerator
Γ-butyrolactoneGenerator
1-Oxacyclopentan-2-oneHMDB
2,3,4,5-Tetrahydro-2-furanoneHMDB
2-OxolanoneHMDB
2-OxotetrahydrofuranHMDB
4,5-Dihydro-2(3H)-furanoneHMDB
4-ButanolideHMDB
4-Hydroxy-butanoateHMDB
4-Hydroxy-butanoic acidHMDB
4-Hydroxy-butanoic acid g-lactoneHMDB
4-HydroxybutanoateHMDB
4-Hydroxybutanoic acidHMDB
4-Hydroxybutanoic acid lactoneHMDB
Butyric acid lactoneHMDB
g-ButalactoneHMDB
g-ButyryllactoneHMDB
gamma-ButalactoneHMDB
gamma-ButyryllactoneHMDB
GBLHMDB
Paint clean gHMDB
Tetrahydro-2-furanoneHMDB
4 ButyrolactoneHMDB
gamma ButyrolactoneHMDB
Furanone, tetrahydro 2HMDB
1,4 ButanolideHMDB
4 Hydroxybutyric acid lactoneHMDB
Lactone, 4-hydroxybutyric acidHMDB
gamma-ButyrolactoneMeSH
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Nameoxolan-2-one
Traditional Namebutyrolactone
CAS Registry Number96-48-0
SMILES
O=C1CCCO1
InChI Identifier
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
InChI KeyYEJRWHAVMIAJKC-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-45 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-0.64HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.11ALOGPS
logP0.15ChemAxon
logS0.44ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.31 m³·mol⁻¹ChemAxon
Polarizability8.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adipose Tissue
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000549
DrugBank IDDB04699
Phenol Explorer Compound IDNot Available
FooDB IDFDB003392
KNApSAcK IDC00053167
Chemspider ID7029
KEGG Compound IDC01770
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Butyrolactone
METLIN ID5533
PubChem Compound7302
PDB IDNot Available
ChEBI ID42639
References
Synthesis ReferenceZhu, 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 ReferencesNot 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