gamma-butyrolactone

Identification

Name
gamma-butyrolactone
Accession Number
DB04699
Type
Small Molecule
Groups
Experimental
Description

One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent. [PubChem]

Structure
Thumb
Synonyms
  • 1,4-Lactone
  • 4-Butyrolactone
  • 4-Hydroxybutyric acid lactone
  • butyrolactone
  • dihydrofuran-2(3h)-one
  • γ-butyrolactone
External IDs
FEMA NO. 3291 / NSC-4592
Categories
UNII
OL659KIY4X
CAS number
96-48-0
Weight
Average: 86.0892
Monoisotopic: 86.036779436
Chemical Formula
C4H6O2
InChI Key
YEJRWHAVMIAJKC-UHFFFAOYSA-N
InChI
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
IUPAC Name
oxolan-2-one
SMILES
O=C1CCCO1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UO-GlcNAcase NagJNot AvailableClostridium perfringens (strain 13 / Type A)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Fabio Giannessi, Maria Ornella Tinti, Francesco De Angelis, "Process for producing (R)-3-hydroxy-4-butyrolactone useful for preparing (R)-carnitine." U.S. Patent US6127552, issued February, 1998.

US6127552
General References
Not Available
External Links
Human Metabolome Database
HMDB00549
KEGG Compound
C01770
PubChem Compound
7302
PubChem Substance
46508619
ChemSpider
7029
ChEBI
42639
ChEMBL
CHEMBL95681
HET
GBL
Wikipedia
Gamma-Butyrolactone
PDB Entries
2cbi / 2vwd / 2wd1 / 3f66 / 3sfz / 3shf / 4ehq / 4knb / 4r1v

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility238.0 mg/mLALOGPS
logP-0.11ALOGPS
logP0.15ChemAxon
logS0.44ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.31 m3·mol-1ChemAxon
Polarizability8.23 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.9837
Caco-2 permeable+0.6346
P-glycoprotein substrateNon-substrate0.8319
P-glycoprotein inhibitor INon-inhibitor0.9572
P-glycoprotein inhibitor IINon-inhibitor0.9896
Renal organic cation transporterNon-inhibitor0.8004
CYP450 2C9 substrateNon-substrate0.8264
CYP450 2D6 substrateNon-substrate0.8742
CYP450 3A4 substrateNon-substrate0.7067
CYP450 1A2 substrateNon-inhibitor0.8028
CYP450 2C9 inhibitorNon-inhibitor0.8599
CYP450 2D6 inhibitorNon-inhibitor0.9398
CYP450 2C19 inhibitorNon-inhibitor0.8187
CYP450 3A4 inhibitorNon-inhibitor0.9841
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9591
Ames testNon AMES toxic0.948
CarcinogenicityNon-carcinogens0.9049
BiodegradationReady biodegradable0.9342
Rat acute toxicity1.7154 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.918
hERG inhibition (predictor II)Non-inhibitor0.97
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-004l-9000000000-500445dc73cb69119e6b
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1
GC-MS Spectrum - EI-BGC-MSsplash10-002f-9000000000-d3df175d3315ed446e14
Mass Spectrum (Electron Ionization)MSsplash10-004l-9000000000-2fc3f4165b5808b41e93
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-4a6de93563809aa51a33
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-4a6de93563809aa51a33
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-b5163f6eb1e8004e61a9
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-004l-9000000000-1066d349a6023c66dd64
MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , PositiveLC-MS/MSsplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-002f-9000000000-d3df175d3315ed446e14
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as gamma butyrolactones. These 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
Tetrahydrofurans / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Gamma butyrolactone / Tetrahydrofuran / Carboxylic acid ester / Oxacycle / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
butan-4-olide (CHEBI:42639) / Lactones (LMFA07040004)

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
Unknown
General Function
Carbohydrate binding
Specific Function
Binds carbohydrates. Capable of hydrolyzing the glycosidic link of O-GlcNAcylated proteins. Can bind and deglycosylate O-glycosylated peptides from mammals. Can use p-nitrophenyl-beta-GlcNAc and 4-...
Gene Name
nagJ
Uniprot ID
Q8XL08
Uniprot Name
O-GlcNAcase NagJ
Molecular Weight
111107.99 Da

Drug created on September 11, 2007 11:49 / Updated on November 09, 2017 03:45