Identification
- Generic Name
- trans-urocanic acid
- DrugBank Accession Number
- DB01971
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for trans-urocanic acid (DB01971)
- Weight
- Average: 138.124
Monoisotopic: 138.042927446 - Chemical Formula
- C6H6N2O2
- Synonyms
- (2E)-3-(1H-imidazol-4-yl)acrylic acid
- (E)-3-(1H-imidazol-4-yl)-2-propenoic acid
- Urocanic acid
- External IDs
- 104-98-3
- NSC-66357
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UUrocanate hydratase Not Available Pseudomonas putida (strain KT2440) - 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
Pathway Category Ammonia Recycling Metabolic Histidine Metabolism Metabolic Histidinemia Disease - 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 imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Imidazoles
- Direct Parent
- Imidazolyl carboxylic acids and derivatives
- Alternative Parents
- Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidazolyl carboxylic acid derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- urocanic acid (CHEBI:30817)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- G8D26XJJ3B
- CAS number
- 3465-72-3
- InChI Key
- LOIYMIARKYCTBW-OWOJBTEDSA-N
- InChI
- InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
- IUPAC Name
- (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
- SMILES
- OC(=O)\C=C\C1=CNC=N1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000301
- KEGG Compound
- C00785
- PubChem Compound
- 736715
- PubChem Substance
- 46504955
- ChemSpider
- 643824
- ChEBI
- 30817
- ChEMBL
- CHEMBL1236602
- ZINC
- ZINC000034633903
- PDBe Ligand
- URO
- Wikipedia
- Urocanic_acid
- PDB Entries
- 1uwk / 1w1u / 6t87 / 7ned
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) 225 °C PhysProp water solubility 1500 mg/L (at 17 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 42.5 mg/mL ALOGPS logP 0.22 ALOGPS logP -1 Chemaxon logS -0.51 ALOGPS pKa (Strongest Acidic) 3.66 Chemaxon pKa (Strongest Basic) 6.13 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 65.98 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 35.57 m3·mol-1 Chemaxon Polarizability 13.1 Å3 Chemaxon Number of Rings 1 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 + 0.9808 Blood Brain Barrier + 0.9668 Caco-2 permeable - 0.5954 P-glycoprotein substrate Non-substrate 0.7113 P-glycoprotein inhibitor I Non-inhibitor 0.9759 P-glycoprotein inhibitor II Non-inhibitor 0.9665 Renal organic cation transporter Non-inhibitor 0.9003 CYP450 2C9 substrate Non-substrate 0.8308 CYP450 2D6 substrate Non-substrate 0.8775 CYP450 3A4 substrate Non-substrate 0.8582 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9103 CYP450 2D6 inhibitor Non-inhibitor 0.9276 CYP450 2C19 inhibitor Non-inhibitor 0.9165 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9566 Ames test Non AMES toxic 0.9142 Carcinogenicity Non-carcinogens 0.8833 Biodegradation Not ready biodegradable 0.6566 Rat acute toxicity 2.2756 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.982 hERG inhibition (predictor II) Non-inhibitor 0.9803
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 128.4023241 predictedDarkChem Lite v0.1.0 [M-H]- 135.2789285 predictedDarkChem Standard v0.1.0 [M-H]- 130.5742241 predictedDarkChem Lite v0.1.0 [M-H]- 128.2855241 predictedDarkChem Lite v0.1.0 [M-H]- 124.5968 predictedDeepCCS 1.0 (2019) [M+H]+ 129.1712241 predictedDarkChem Lite v0.1.0 [M+H]+ 135.9435832 predictedDarkChem Standard v0.1.0 [M+H]+ 131.3573241 predictedDarkChem Lite v0.1.0 [M+H]+ 129.0839241 predictedDarkChem Lite v0.1.0 [M+H]+ 127.62117 predictedDeepCCS 1.0 (2019) [M+Na]+ 128.8604241 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.5496241 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.5249241 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.0907241 predictedDarkChem Lite v0.1.0 [M+Na]+ 136.75433 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Pseudomonas putida (strain KT2440)
- Pharmacological action
- Unknown
- General Function
- Urocanate hydratase activity
- Specific Function
- Not Available
- Gene Name
- hutU
- Uniprot ID
- Q88CZ6
- Uniprot Name
- Urocanate hydratase
- Molecular Weight
- 60717.31 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52