NAV

gamma-Butyrolactone

Identification

Generic Name
gamma-Butyrolactone
DrugBank Accession Number
DB04699
Background

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.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 86.0892
Monoisotopic: 86.036779436
Chemical Formula
C4H6O2
Synonyms
  • 1,4-lactone
  • 4-butyrolactone
  • 4-hydroxybutyric acid lactone
  • butyrolactone
  • dihydrofuran-2(3h)-one
  • GBL
  • γ-butyrolactone
External IDs
  • FEMA NO. 3291
  • NSC-4592
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Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic heteromonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Gamma butyrolactone / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
butan-4-olide (CHEBI:42639) / Lactones (LMFA07040004)
Affected organisms
Not Available

Chemical Identifiers

UNII
OL659KIY4X
CAS number
96-48-0
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

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
Human Metabolome Database
HMDB0000549
KEGG Compound
C01770
PubChem Compound
7302
PubChem Substance
46508619
ChemSpider
7029
ChEBI
42639
ChEMBL
CHEMBL95681
ZINC
ZINC000004658567
PDBe Ligand
GBL
Wikipedia
Gamma-Butyrolactone
PDB Entries
2cbi / 2vwd / 2wd1 / 3f66 / 3sfz / 3shf / 4ehq / 4knb / 4r1v / 7d9x

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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-MSsplash10-002f-9000000000-bd4b413f20907d13a107
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/MSsplash10-00ku-9000000000-0f7d12344a1d06bc392b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-dec19e876eee9d4bb6f3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052u-9000000000-d185c883adc007c59d3b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-d3f3faa56a27bd38674b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-3cebcc00fb4e478e41f3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-f6401aa62f93aa0ad7a0
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-105.6988043
predicted
DarkChem Lite v0.1.0
[M-H]-105.7809043
predicted
DarkChem Lite v0.1.0
[M-H]-105.8007043
predicted
DarkChem Lite v0.1.0
[M-H]-105.7928043
predicted
DarkChem Lite v0.1.0
[M-H]-122.69838
predicted
DeepCCS 1.0 (2019)
[M+H]+106.6894043
predicted
DarkChem Lite v0.1.0
[M+H]+106.6431043
predicted
DarkChem Lite v0.1.0
[M+H]+106.6416043
predicted
DarkChem Lite v0.1.0
[M+H]+106.7713043
predicted
DarkChem Lite v0.1.0
[M+H]+124.59379
predicted
DeepCCS 1.0 (2019)
[M+Na]+106.0527043
predicted
DarkChem Lite v0.1.0
[M+Na]+106.0808043
predicted
DarkChem Lite v0.1.0
[M+Na]+106.1775043
predicted
DarkChem Lite v0.1.0
[M+Na]+106.0324043
predicted
DarkChem Lite v0.1.0
[M+Na]+132.6785
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. O-GlcNAcase NagJ
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 at September 11, 2007 17:49 / Updated at October 16, 2020 03:34