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Identification
Name4-Butyrolactone
Accession NumberDB04699
TypeSmall Molecule
GroupsExperimental
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
SynonymLanguageCode
1,4-LactoneNot AvailableNot Available
dihydrofuran-2(3h)-oneNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number187997-16-6
WeightAverage: 86.0892
Monoisotopic: 86.036779436
Chemical FormulaC4H6O2
InChI KeyYEJRWHAVMIAJKC-UHFFFAOYSA-N
InChI
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
IUPAC Name
oxolan-2-one
SMILES
O=C1CCCO1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Oxolane
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8599
CYP450 2D6 substrateNon-inhibitor0.9398
CYP450 2C19 substrateNon-inhibitor0.8187
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS/MSMS1D NMR2D NMR
References
Synthesis Reference

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

US6127552
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. O-GlcNAcase NagJ

Kind: protein

Organism: Clostridium perfringens (strain 13 / Type A)

Pharmacological action: unknown

Components

Name UniProt ID Details
O-GlcNAcase NagJ Q8XL08 Details
Comments
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Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25