3-{ISOPROPYL[(TRANS-4-METHYLCYCLOHEXYL)CARBONYL]AMINO}-5-PHENYLTHIOPHENE-2-CARBOXYLIC ACID

Identification

Name
3-{ISOPROPYL[(TRANS-4-METHYLCYCLOHEXYL)CARBONYL]AMINO}-5-PHENYLTHIOPHENE-2-CARBOXYLIC ACID
Accession Number
DB08279
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: 385.52
Monoisotopic: 385.171164425
Chemical Formula
C22H27NO3S
InChI Key
RZXQBIKGWSLVEK-JCNLHEQBSA-N
InChI
InChI=1S/C22H27NO3S/c1-14(2)23(21(24)17-11-9-15(3)10-12-17)18-13-19(27-20(18)22(25)26)16-7-5-4-6-8-16/h4-8,13-15,17H,9-12H2,1-3H3,(H,25,26)/t15-,17-
IUPAC Name
5-phenyl-3-[N-(propan-2-yl)(1r,4r)-4-methylcyclohexaneamido]thiophene-2-carboxylic acid
SMILES
[H][C@]1(C)CC[C@@]([H])(CC1)C(=O)N(C(C)C)C1=C(SC(=C1)C1=CC=CC=C1)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
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
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
PubChem Compound
503536
PubChem Substance
99444750
ChemSpider
24626592
BindingDB
35554
ChEMBL
CHEMBL561360
ZINC
ZINC000100036573
PDBe Ligand
NN3
PDB Entries
2gir / 4jy1

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 Solubility0.00121 mg/mLALOGPS
logP4.68ALOGPS
logP5.46ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.02 m3·mol-1ChemAxon
Polarizability43.51 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9827
Blood Brain Barrier+0.7329
Caco-2 permeable+0.5325
P-glycoprotein substrateNon-substrate0.7489
P-glycoprotein inhibitor INon-inhibitor0.6353
P-glycoprotein inhibitor IIInhibitor0.7781
Renal organic cation transporterNon-inhibitor0.9122
CYP450 2C9 substrateNon-substrate0.5
CYP450 2D6 substrateNon-substrate0.8065
CYP450 3A4 substrateSubstrate0.5319
CYP450 1A2 substrateNon-inhibitor0.6644
CYP450 2C9 inhibitorNon-inhibitor0.5204
CYP450 2D6 inhibitorNon-inhibitor0.8787
CYP450 2C19 inhibitorInhibitor0.6102
CYP450 3A4 inhibitorNon-inhibitor0.6589
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.7109
CarcinogenicityNon-carcinogens0.685
BiodegradationNot ready biodegradable0.9529
Rat acute toxicity2.4734 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.997
hERG inhibition (predictor II)Non-inhibitor0.7532
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 thiophene carboxylic acids. These are compounds containing a thiophene ring which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiophenes
Sub Class
Thiophene carboxylic acids and derivatives
Direct Parent
Thiophene carboxylic acids
Alternative Parents
2,3,5-trisubstituted thiophenes / Benzene and substituted derivatives / Vinylogous amides / Tertiary carboxylic acid amides / Heteroaromatic compounds / Carboxylic acids / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Thiophene carboxylic acid / 2,3,5-trisubstituted thiophene / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide / Vinylogous amide / Heteroaromatic compound / Carboxamide group / Carboxylic acid / Carboxylic acid derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Hepatitis C virus genotype 1b (isolate BK)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Core protein packages viral RNA to form a viral nucleocapsid, and promotes virion budding. Modulates viral translation initiation by interacting with HCV IRES and 40S ribosomal subunit. Also regula...
Gene Name
Not Available
Uniprot ID
P26663
Uniprot Name
Genome polyprotein
Molecular Weight
327190.435 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 15:30 / Updated on March 01, 2020 20:14

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