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Identification
NameLaevulinic Acid
Accession NumberDB02239  (EXPT02901)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number123-76-2
WeightAverage: 116.1152
Monoisotopic: 116.047344122
Chemical FormulaC5H8O3
InChI KeyJOOXCMJARBKPKM-UHFFFAOYSA-N
InChI
InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
IUPAC Name
4-oxopentanoic acid
SMILES
CC(=O)CCC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Short-chain keto acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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+0.9817
Blood Brain Barrier+0.9511
Caco-2 permeable+0.613
P-glycoprotein substrateNon-substrate0.6921
P-glycoprotein inhibitor INon-inhibitor0.9346
P-glycoprotein inhibitor IINon-inhibitor0.9537
Renal organic cation transporterNon-inhibitor0.9327
CYP450 2C9 substrateNon-substrate0.7857
CYP450 2D6 substrateNon-substrate0.8982
CYP450 3A4 substrateNon-substrate0.7269
CYP450 1A2 substrateNon-inhibitor0.6354
CYP450 2C9 substrateNon-inhibitor0.9704
CYP450 2D6 substrateNon-inhibitor0.9663
CYP450 2C19 substrateNon-inhibitor0.97
CYP450 3A4 substrateNon-inhibitor0.9773
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9927
Ames testNon AMES toxic0.9638
CarcinogenicityNon-carcinogens0.721
BiodegradationReady biodegradable0.9713
Rat acute toxicity1.7665 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9476
hERG inhibition (predictor II)Non-inhibitor0.9668
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point33 °CPhysProp
boiling point245.5 °CPhysProp
logP-0.49HANSCH,C ET AL. (1995)
pKa4.64 (at 18 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility139.0 mg/mLALOGPS
logP-0.14ALOGPS
logP-0.069ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.09 m3·mol-1ChemAxon
Polarizability11.23 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis Reference

Bernard Capai, Guy Lartigau, “Preparation of laevulinic acid.” U.S. Patent US5175358, issued December, 1939.

US5175358
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Delta-aminolevulinic acid dehydratase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Delta-aminolevulinic acid dehydratase P13716 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17