Laevulinic Acid

Identification

Name
Laevulinic Acid
Accession Number
DB02239  (EXPT02901)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 2627
Categories
Not Available
UNII
RYX5QG61EI
CAS number
123-76-2
Weight
Average: 116.1152
Monoisotopic: 116.047344122
Chemical Formula
C5H8O3
InChI Key
JOOXCMJARBKPKM-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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDelta-aminolevulinic acid dehydrataseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

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

US5175358
General References
Not Available
External Links
Human Metabolome Database
HMDB00720
PubChem Compound
11579
PubChem Substance
46504792
ChemSpider
11091
BindingDB
82191
ChEBI
45630
ChEMBL
CHEMBL1235931
HET
SHF
Wikipedia
Laevulinic_Acid
PDB Entries
1b4e / 1b4k / 1h7n / 1w1z / 1ylv / 2xua

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)33 °CPhysProp
boiling point (°C)245.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9704
CYP450 2D6 inhibitorNon-inhibitor0.9663
CYP450 2C19 inhibitorNon-inhibitor0.97
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-0ug0-6900000000-1e5d9b8d9a359287a6b0
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-0ug0-6900000000-ffad5af79457e68cca02
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-dd0d17209893b2b71d10
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-0b0447e3daa65b1cd932
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-e0d39a4a978220036faa
GC-MS Spectrum - GC-MSGC-MSsplash10-0ug0-6900000000-1e5d9b8d9a359287a6b0
GC-MS Spectrum - GC-MSGC-MSsplash10-0ug0-6900000000-ffad5af79457e68cca02
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00xr-9400000000-923a1fccce36ba18d088
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-01vo-9300000000-2c09d37e792efac90655
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0303-9800000000-d158f0c32e82eca0ef90
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-0006-9000000000-dd0d17209893b2b71d10
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Keto acids and derivatives
Sub Class
Gamma-keto acids and derivatives
Direct Parent
Gamma-keto acids and derivatives
Alternative Parents
Short-chain keto acids and derivatives / Ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Gamma-keto acid / Short-chain keto acid / Ketone / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
oxopentanoic acid, straight-chain saturated fatty acid (CHEBI:45630) / Oxo fatty acids (LMFA01060006)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name
ALAD
Uniprot ID
P13716
Uniprot Name
Delta-aminolevulinic acid dehydratase
Molecular Weight
36294.485 Da
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:17139284]
  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:17016423]
  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:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:11