2-({[3,5-DIFLUORO-3'-(TRIFLUOROMETHOXY)BIPHENYL-4-YL]AMINO}CARBONYL)CYCLOPENT-1-ENE-1-CARBOXYLIC ACID

Identification

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Name
2-({[3,5-DIFLUORO-3'-(TRIFLUOROMETHOXY)BIPHENYL-4-YL]AMINO}CARBONYL)CYCLOPENT-1-ENE-1-CARBOXYLIC ACID
Accession Number
DB07975
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 427.3215
Monoisotopic: 427.084298966
Chemical Formula
C20H14F5NO4
InChI Key
VTGXLCZUWFYELR-UHFFFAOYSA-N
InChI
InChI=1S/C20H14F5NO4/c21-15-8-11(10-3-1-4-12(7-10)30-20(23,24)25)9-16(22)17(15)26-18(27)13-5-2-6-14(13)19(28)29/h1,3-4,7-9H,2,5-6H2,(H,26,27)(H,28,29)
IUPAC Name
2-({2,6-difluoro-4-[3-(trifluoromethoxy)phenyl]phenyl}carbamoyl)cyclopent-1-ene-1-carboxylic acid
SMILES
OC(=O)C1=C(CCC1)C(=O)NC1=C(F)C=C(C=C1F)C1=CC=CC(OC(F)(F)F)=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydroorotate dehydrogenase (quinone), mitochondrialNot AvailableHumans
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

General References
Not Available
External Links
PubChem Compound
10342449
PubChem Substance
99444446
ChemSpider
8517908
BindingDB
15343
ChEMBL
CHEMBL157105
HET
ILB
PDB Entries
2fpt

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0044 mg/mLALOGPS
logP4.48ALOGPS
logP5.53ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.63 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.04 m3·mol-1ChemAxon
Polarizability37.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9586
Blood Brain Barrier+0.9143
Caco-2 permeable-0.5912
P-glycoprotein substrateNon-substrate0.5924
P-glycoprotein inhibitor INon-inhibitor0.779
P-glycoprotein inhibitor IINon-inhibitor0.7552
Renal organic cation transporterNon-inhibitor0.9091
CYP450 2C9 substrateNon-substrate0.8267
CYP450 2D6 substrateNon-substrate0.8197
CYP450 3A4 substrateSubstrate0.5766
CYP450 1A2 substrateNon-inhibitor0.5881
CYP450 2C9 inhibitorNon-inhibitor0.5395
CYP450 2D6 inhibitorNon-inhibitor0.8925
CYP450 2C19 inhibitorNon-inhibitor0.6155
CYP450 3A4 inhibitorNon-inhibitor0.905
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6736
Ames testNon AMES toxic0.7558
CarcinogenicityNon-carcinogens0.8751
BiodegradationNot ready biodegradable0.9526
Rat acute toxicity2.5439 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.977
hERG inhibition (predictor II)Non-inhibitor0.5263
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
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Anilides / N-arylamides / Phenol ethers / Phenoxy compounds / Fluorobenzenes / Aryl fluorides / Trihalomethanes / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids
show 6 more
Substituents
Biphenyl / Anilide / Phenoxy compound / N-arylamide / Phenol ether / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Carboxamide group
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquinone binding
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name
DHODH
Uniprot ID
Q02127
Uniprot Name
Dihydroorotate dehydrogenase (quinone), mitochondrial
Molecular Weight
42866.93 Da
References
  1. 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 September 15, 2010 15:27 / Updated on June 04, 2019 06:50