trans-urocanic acid

Identification

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Name
trans-urocanic acid
Accession Number
DB01971  (EXPT03207)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
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
Categories
UNII
G8D26XJJ3B
CAS number
3465-72-3
Weight
Average: 138.124
Monoisotopic: 138.042927446
Chemical Formula
C6H6N2O2
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUrocanate hydrataseNot AvailablePseudomonas 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Ammonia RecyclingMetabolic
Histidine MetabolismMetabolic
HistidinemiaDisease
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

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
HET
URO
Wikipedia
Urocanic_acid
PDB Entries
1uwk / 1w1u

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)225 °CPhysProp
water solubility1500 mg/L (at 17 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility42.5 mg/mLALOGPS
logP0.22ALOGPS
logP-1ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
pKa (Strongest Basic)6.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.57 m3·mol-1ChemAxon
Polarizability13.1 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9808
Blood Brain Barrier+0.9668
Caco-2 permeable-0.5954
P-glycoprotein substrateNon-substrate0.7113
P-glycoprotein inhibitor INon-inhibitor0.9759
P-glycoprotein inhibitor IINon-inhibitor0.9665
Renal organic cation transporterNon-inhibitor0.9003
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.8775
CYP450 3A4 substrateNon-substrate0.8582
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9103
CYP450 2D6 inhibitorNon-inhibitor0.9276
CYP450 2C19 inhibitorNon-inhibitor0.9165
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9566
Ames testNon AMES toxic0.9142
CarcinogenicityNon-carcinogens0.8833
BiodegradationNot ready biodegradable0.6566
Rat acute toxicity2.2756 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.982
hERG inhibition (predictor II)Non-inhibitor0.9803
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-014m-1930000000-25b091170cc3ea73bcf7
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00l5-1930000000-5c3c875338a517d52729
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9410000000-b58e1b2cdd5c12a6ba24
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0159-3950000000-433e50271e182f8408fd
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000f-9200000000-cb7f9025a0f6adf740c1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014m-1930000000-25b091170cc3ea73bcf7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00l5-1930000000-5c3c875338a517d52729
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9410000000-b58e1b2cdd5c12a6ba24
GC-MS Spectrum - GC-MSGC-MSsplash10-0159-3950000000-433e50271e182f8408fd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014m-1930000000-3815ef1f1f386e091dc3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dm-2900000000-aaefc749352097679e8f
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-3900000000-8c1c060d06c1ce3fb5f7
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00kf-9000000000-ae9de21d4642045fb96c
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014l-9000000000-8e6978d7f104386d2e82
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-000f-9200000000-cb7f9025a0f6adf740c1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-1900000000-c628b05706544cb1ebdc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0006-9300000000-bc4c631410a5cbb3c2f5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9000000000-ccac569cbc78a632da48
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-a22c861e4f2551a3f582
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00kf-9000000000-37421b473ba575d307fd
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00du-5900000000-29dc15087c785a19c0ee
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0006-9200000000-1cc9b0a66b83ca383ebd
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-1900000000-c628b05706544cb1ebdc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9300000000-bc4c631410a5cbb3c2f5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-ccac569cbc78a632da48
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-a22c861e4f2551a3f582
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-9000000000-37421b473ba575d307fd
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-9200000000-1cc9b0a66b83ca383ebd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00du-5900000000-29dc15087c785a19c0ee
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 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
Imidazolyl carboxylic acid derivative / Heteroaromatic compound / Azacycle / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
urocanic acid (CHEBI:30817)

Targets

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
  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]

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 17:12