Citraconic acid
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Identification
- Generic Name
- Citraconic acid
- DrugBank Accession Number
- DB04734
- Background
Citraconic acid is one of the isomeric dicarboxylic acids produced by the distillation of citric acid, or as metabolites by microorganisms, cis-CH3-C(CO2H)=CHCO2H; the trans-isomer is mesaconic acid.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 130.0987
Monoisotopic: 130.02660868 - Chemical Formula
- C5H6O4
- Synonyms
- (Z)-2-Methyl-2-butenedioic acid
- 2-Methyl-2-butenedioic acid
- 2-methylmaleic acid
- cis-2-methylbutenedioic acid
- cis-Methylbutenedioic acid
- citraconate
- Citraconsäure
- Methyl-maleinsäure
- Methylmaleic acid
- α-methylmaleic acid
- External IDs
- NSC-32949
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UFumarate reductase flavoprotein subunit Not Available Shewanella frigidimarina - 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
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Methyl-branched fatty acids
- Alternative Parents
- Unsaturated fatty acids / Dicarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Hydrocarbon derivative / Methyl-branched fatty acid / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- dicarboxylic acid (CHEBI:17626) / Dicarboxylic acids (LMFA01170099)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0RQ6CXO9KD
- CAS number
- 498-23-7
- InChI Key
- HNEGQIOMVPPMNR-IHWYPQMZSA-N
- InChI
- InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
- IUPAC Name
- (2Z)-2-methylbut-2-enedioic acid
- SMILES
- C\C(=C\C(O)=O)C(O)=O
References
- Synthesis Reference
Chiyuki Fujii, Yoshio Kosai, Iwao Kibayashi, "Method for preparation of citraconic acid and derivatives thereof." U.S. Patent US3931241, issued November, 1973.
US3931241- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000634
- KEGG Compound
- C02226
- PubChem Compound
- 643798
- PubChem Substance
- 46505839
- ChemSpider
- 553689
- 1435287
- ChEBI
- 17626
- ZINC
- ZINC000003860287
- PDBe Ligand
- CIZ
- Wikipedia
- Citraconic_acid
- PDB Entries
- 5kts
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 93.5 °C PhysProp water solubility 7.83E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 15.9 mg/mL ALOGPS logP 0.21 ALOGPS logP 0.35 Chemaxon logS -0.91 ALOGPS pKa (Strongest Acidic) 2.31 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 28.96 m3·mol-1 Chemaxon Polarizability 11.17 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 + 0.9004 Blood Brain Barrier + 0.6692 Caco-2 permeable - 0.6516 P-glycoprotein substrate Non-substrate 0.6757 P-glycoprotein inhibitor I Non-inhibitor 0.9646 P-glycoprotein inhibitor II Non-inhibitor 0.9843 Renal organic cation transporter Non-inhibitor 0.9497 CYP450 2C9 substrate Non-substrate 0.8227 CYP450 2D6 substrate Non-substrate 0.9331 CYP450 3A4 substrate Non-substrate 0.7247 CYP450 1A2 substrate Non-inhibitor 0.9489 CYP450 2C9 inhibitor Non-inhibitor 0.8722 CYP450 2D6 inhibitor Non-inhibitor 0.9392 CYP450 2C19 inhibitor Non-inhibitor 0.9528 CYP450 3A4 inhibitor Non-inhibitor 0.9684 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9701 Ames test Non AMES toxic 0.8707 Carcinogenicity Non-carcinogens 0.5089 Biodegradation Ready biodegradable 0.869 Rat acute toxicity 1.9626 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9697 hERG inhibition (predictor II) Non-inhibitor 0.9826
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 124.6180461 predictedDarkChem Lite v0.1.0 [M-H]- 124.5732461 predictedDarkChem Lite v0.1.0 [M-H]- 120.779594 predictedDeepCCS 1.0 (2019) [M+H]+ 124.61038 predictedDeepCCS 1.0 (2019) [M+Na]+ 133.63345 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsFumarate reductase flavoprotein subunit
- Kind
- Protein
- Organism
- Shewanella frigidimarina
- Pharmacological action
- Unknown
- General Function
- Succinate dehydrogenase activity
- Specific Function
- Catalyzes fumarate reduction using artificial electron donors such as methyl viologen. The physiological reductant is unknown, but evidence indicates that flavocytochrome c participates in electron...
- Gene Name
- fccA
- Uniprot ID
- P0C278
- Uniprot Name
- Fumarate reductase flavoprotein subunit
- Molecular Weight
- 60620.95 Da
Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52