(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID

Identification

Name
(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID
Accession Number
DB07200
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: 469.474
Monoisotopic: 469.117078124
Chemical Formula
C22H22F3NO5S
InChI Key
ZNCZVHCYBGHCHA-XPIZARPCSA-N
InChI
InChI=1S/C22H22F3NO5S/c1-12(2)10-21(20(30)31)11-15(19(28)29)17(16-4-3-9-32-16)26(21)18(27)13-5-7-14(8-6-13)22(23,24)25/h3-9,12,15,17H,10-11H2,1-2H3,(H,28,29)(H,30,31)/t15-,17+,21-/m0/s1
IUPAC Name
(2S,4S,5R)-2-(2-methylpropyl)-5-(thiophen-2-yl)-1-[4-(trifluoromethyl)benzoyl]pyrrolidine-2,4-dicarboxylic acid
SMILES
[H][C@@]1(C[C@](CC(C)C)(N(C(=O)C2=CC=C(C=C2)C(F)(F)F)[C@@]1([H])C1=CC=CS1)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
URNA-dependent RNA-polymeraseNot AvailableHepatitis C Virus
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
5275422
PubChem Substance
99443671
ChemSpider
4439526
BindingDB
50162519
ChEMBL
CHEMBL180948
ZINC
ZINC000016052233
PDBe Ligand
699
PDB Entries
2jc0

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 Solubility0.00317 mg/mLALOGPS
logP3.51ALOGPS
logP5.01ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-0.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.91 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity109.92 m3·mol-1ChemAxon
Polarizability42.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.996
Blood Brain Barrier+0.5059
Caco-2 permeable-0.5898
P-glycoprotein substrateNon-substrate0.6799
P-glycoprotein inhibitor INon-inhibitor0.8589
P-glycoprotein inhibitor IINon-inhibitor0.5542
Renal organic cation transporterNon-inhibitor0.9523
CYP450 2C9 substrateNon-substrate0.7552
CYP450 2D6 substrateNon-substrate0.8068
CYP450 3A4 substrateSubstrate0.5064
CYP450 1A2 substrateNon-inhibitor0.8283
CYP450 2C9 inhibitorNon-inhibitor0.7096
CYP450 2D6 inhibitorNon-inhibitor0.9125
CYP450 2C19 inhibitorNon-inhibitor0.5992
CYP450 3A4 inhibitorNon-inhibitor0.9058
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7345
Ames testNon AMES toxic0.7931
CarcinogenicityNon-carcinogens0.7417
BiodegradationNot ready biodegradable0.9953
Rat acute toxicity2.4526 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9993
hERG inhibition (predictor II)Non-inhibitor0.7973
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 n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids
Alternative Parents
Trifluoromethylbenzenes / Benzamides / Pyrrolidine carboxylic acids / Benzoyl derivatives / N-acylpyrrolidines / Dicarboxylic acids and derivatives / Thiophenes / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azacyclic compounds
show 8 more
Substituents
N-acyl-alpha-amino acid / Trifluoromethylbenzene / Benzamide / Benzoic acid or derivatives / Benzoyl / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine carboxylic acid / N-acylpyrrolidine / Monocyclic benzene moiety / Dicarboxylic acid or derivatives
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiophenes, dicarboxylic acid, N-acylpyrrolidine, pyrrolidinedicarboxylic acid (CHEBI:40197)

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]
Kind
Protein
Organism
Hepatitis C Virus
Pharmacological action
Unknown
General Function
Rna-directed rna polymerase activity
Specific Function
Not Available
Gene Name
NS5b
Uniprot ID
O39930
Uniprot Name
RNA-dependent RNA-polymerase
Molecular Weight
65753.05 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 15:19 / Updated on March 01, 2020 19:53

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