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

Identification

Generic Name
3-{ISOPROPYL[(TRANS-4-METHYLCYCLOHEXYL)CARBONYL]AMINO}-5-PHENYLTHIOPHENE-2-CARBOXYLIC ACID
DrugBank Accession Number
DB08279
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 385.52
Monoisotopic: 385.171164425
Chemical Formula
C22H27NO3S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

Adverse Effects
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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
Not Available
Chemical TaxonomyProvided by Classyfire
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
2,3,5-trisubstituted thiophene / Aromatic heteromonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
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
PhaseStatusPurposeConditionsCount

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/MSsplash10-000i-0009000000-80845a45dffa6f8ccf1c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0019000000-14daa423178e025ae217
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2019000000-e661e9a7aadc727dc11f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0149000000-94e430e317c6bd8b5689
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-9001000000-ec9def65a6d8eb853300
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-008a-2977000000-e3c884cdc2f55a78ed82
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.36317
predicted
DeepCCS 1.0 (2019)
[M+H]+195.75874
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.70767
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52