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Identification
Namegamma-butyrolactone
Accession NumberDB04699
TypeSmall Molecule
GroupsExperimental
DescriptionOne 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 Identifiers
  • FEMA NO. 3291
  • NSC-4592
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIOL659KIY4X
CAS number96-48-0
WeightAverage: 86.0892
Monoisotopic: 86.036779436
Chemical FormulaC4H6O2
InChI KeyInChIKey=YEJRWHAVMIAJKC-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
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 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 )
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-4a6de93563809aa51a33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-4a6de93563809aa51a33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-b5163f6eb1e8004e61a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-004l-9000000000-1066d349a6023c66dd64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-002f-9000000000-d3df175d3315ed446e14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-2fc3f4165b5808b41e93View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 ReferencesNot 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

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-methylumbelliferone-GlcNAc as substrates (in vitro).
Gene Name:
nagJ
Uniprot ID:
Q8XL08
Molecular Weight:
111107.99 Da
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24