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Identification
NameLaevulinic Acid
Accession NumberDB02239  (EXPT02901)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassKeto-Acids and Derivatives
SubclassGamma Keto-Acids and Derivatives
Direct parentGamma Keto-Acids and Derivatives
Alternative parentsKetones; Polyamines; Enolates; Carboxylic Acids; Keto Acids and Derivatives
Substituentsketo acid; ketone; polyamine; enolate; carboxylic acid derivative; carboxylic acid; carbonyl group
Classification descriptionThis compound belongs to the gamma keto-acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
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
Property Value Probability
Human Intestinal Absorption + 0.9817
Blood Brain Barrier + 0.9511
Caco-2 permeable + 0.613
P-glycoprotein substrate Non-substrate 0.6921
P-glycoprotein inhibitor I Non-inhibitor 0.9346
P-glycoprotein inhibitor II Non-inhibitor 0.9537
Renal organic cation transporter Non-inhibitor 0.9327
CYP450 2C9 substrate Non-substrate 0.7857
CYP450 2D6 substrate Non-substrate 0.8982
CYP450 3A4 substrate Non-substrate 0.7269
CYP450 1A2 substrate Non-inhibitor 0.6354
CYP450 2C9 substrate Non-inhibitor 0.9704
CYP450 2D6 substrate Non-inhibitor 0.9663
CYP450 2C19 substrate Non-inhibitor 0.97
CYP450 3A4 substrate Non-inhibitor 0.9773
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9927
Ames test Non AMES toxic 0.9638
Carcinogenicity Non-carcinogens 0.721
Biodegradation Ready biodegradable 0.9713
Rat acute toxicity 1.7665 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9476
hERG inhibition (predictor II) Non-inhibitor 0.9668
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 solubility1.39e+02 g/lALOGPS
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 area54.37ChemAxon
rotatable bond count3ChemAxon
refractivity27.09ChemAxon
polarizability11.23ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
PubChem Compound11579
PubChem Substance46504792
ChemSpider11091
ChEBI39149
ChEMBL
HETSHF
WikipediaLaevulinic_Acid
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