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
Structure for gamma-Butyrolactone (DB04699)
- 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
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UO-GlcNAcase NagJ Not Available Clostridium 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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
- External Links
- 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
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
Property Value Source Water Solubility 238.0 mg/mL ALOGPS 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9894 Blood Brain Barrier + 0.9837 Caco-2 permeable + 0.6346 P-glycoprotein substrate Non-substrate 0.8319 P-glycoprotein inhibitor I Non-inhibitor 0.9572 P-glycoprotein inhibitor II Non-inhibitor 0.9896 Renal organic cation transporter Non-inhibitor 0.8004 CYP450 2C9 substrate Non-substrate 0.8264 CYP450 2D6 substrate Non-substrate 0.8742 CYP450 3A4 substrate Non-substrate 0.7067 CYP450 1A2 substrate Non-inhibitor 0.8028 CYP450 2C9 inhibitor Non-inhibitor 0.8599 CYP450 2D6 inhibitor Non-inhibitor 0.9398 CYP450 2C19 inhibitor Non-inhibitor 0.8187 CYP450 3A4 inhibitor Non-inhibitor 0.9841 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9591 Ames test Non AMES toxic 0.948 Carcinogenicity Non-carcinogens 0.9049 Biodegradation Ready biodegradable 0.9342 Rat acute toxicity 1.7154 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.918 hERG inhibition (predictor II) Non-inhibitor 0.97
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 105.6988043 predictedDarkChem Lite v0.1.0 [M-H]- 105.7809043 predictedDarkChem Lite v0.1.0 [M-H]- 105.8007043 predictedDarkChem Lite v0.1.0 [M-H]- 105.7928043 predictedDarkChem Lite v0.1.0 [M-H]- 122.69838 predictedDeepCCS 1.0 (2019) [M+H]+ 106.6894043 predictedDarkChem Lite v0.1.0 [M+H]+ 106.6431043 predictedDarkChem Lite v0.1.0 [M+H]+ 106.6416043 predictedDarkChem Lite v0.1.0 [M+H]+ 106.7713043 predictedDarkChem Lite v0.1.0 [M+H]+ 124.59379 predictedDeepCCS 1.0 (2019) [M+Na]+ 106.0527043 predictedDarkChem Lite v0.1.0 [M+Na]+ 106.0808043 predictedDarkChem Lite v0.1.0 [M+Na]+ 106.1775043 predictedDarkChem Lite v0.1.0 [M+Na]+ 106.0324043 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.6785 predictedDeepCCS 1.0 (2019)
Targets
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- 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