Laevulinic Acid
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Identification
- Generic Name
- Laevulinic Acid
- DrugBank Accession Number
- DB02239
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 116.1152
Monoisotopic: 116.047344122 - Chemical Formula
- C5H8O3
- Synonyms
- Not Available
- External IDs
- FEMA NO. 2627
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ADelta-aminolevulinic acid dehydratase inhibitorHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Purus antibacterial wipes Laevulinic Acid (0.028 g/56g) + Caprylhydroxamic acid (0.0112 g/56g) + Ethanol (0.0112 mL/56g) + Glyceryl laurate (0.0448 g/56g) Cloth Topical The fab Korea Co., Ltd. 2020-09-02 Not applicable US Purus antibacterial wipes Laevulinic Acid (0.028 g/56g) + Caprylhydroxamic acid (0.0168 g/56g) + Ethanol (0.0112 mL/56g) + Glyceryl laurate (0.0448 g/56g) Cloth Topical The fab Korea Co., Ltd. 2020-05-04 Not applicable US
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Gamma-keto acid / Hydrocarbon derivative / Ketone / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- oxopentanoic acid, straight-chain saturated fatty acid (CHEBI:45630) / Oxo fatty acids (LMFA01060006)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- RYX5QG61EI
- CAS number
- 123-76-2
- 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
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
- HMDB0000720
- PubChem Compound
- 11579
- PubChem Substance
- 46504792
- ChemSpider
- 11091
- BindingDB
- 82191
- ChEBI
- 45630
- ChEMBL
- CHEMBL1235931
- ZINC
- ZINC000000586584
- PDBe Ligand
- SHF
- Wikipedia
- Laevulinic_Acid
- PDB Entries
- 1b4e / 1b4k / 1h7n / 1w1z / 1ylv / 2xua / 6hjf / 6hjg
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cloth Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 33 °C PhysProp boiling point (°C) 245.5 °C PhysProp logP -0.49 HANSCH,C ET AL. (1995) pKa 4.64 (at 18 °C) KORTUM,G ET AL (1961) - Predicted Properties
Property Value Source Water Solubility 139.0 mg/mL ALOGPS logP -0.14 ALOGPS logP -0.069 Chemaxon logS 0.08 ALOGPS pKa (Strongest Acidic) 4.32 Chemaxon pKa (Strongest Basic) -7.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.37 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 27.09 m3·mol-1 Chemaxon Polarizability 11.23 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9704 CYP450 2D6 inhibitor Non-inhibitor 0.9663 CYP450 2C19 inhibitor Non-inhibitor 0.97 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 121.1393615 predictedDarkChem Lite v0.1.0 [M-H]- 121.0439615 predictedDarkChem Lite v0.1.0 [M-H]- 121.1217615 predictedDarkChem Lite v0.1.0 [M-H]- 121.0843615 predictedDarkChem Lite v0.1.0 [M-H]- 120.65187 predictedDeepCCS 1.0 (2019) [M+H]+ 122.3513615 predictedDarkChem Lite v0.1.0 [M+H]+ 120.7865615 predictedDarkChem Lite v0.1.0 [M+H]+ 119.9570615 predictedDarkChem Lite v0.1.0 [M+H]+ 122.7000615 predictedDarkChem Lite v0.1.0 [M+H]+ 123.42645 predictedDeepCCS 1.0 (2019) [M+Na]+ 120.8588615 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.9297615 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.7739615 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.94972 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDelta-aminolevulinic acid dehydratase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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
- Specific Function
- catalytic activity
- Gene Name
- ALAD
- Uniprot ID
- P13716
- Uniprot Name
- Delta-aminolevulinic acid dehydratase
- Molecular Weight
- 36294.485 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22