NAV

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

Identification

Generic Name
(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID
DrugBank Accession Number
DB07200
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 469.474
Monoisotopic: 469.117078124
Chemical Formula
C22H22F3NO5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 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
Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Carbonyl group / Carboxamide group
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiophenes, dicarboxylic acid, N-acylpyrrolidine, pyrrolidinedicarboxylic acid (CHEBI:40197)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
5275422
PubChem Substance
99443671
ChemSpider
4439526
BindingDB
50162519
ChEMBL
CHEMBL180948
ZINC
ZINC000016052233
PDBe Ligand
699
PDB Entries
2jc0

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 Solubility0.00317 mg/mLALOGPS
logP3.51ALOGPS
logP5.01Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.1Chemaxon
pKa (Strongest Basic)-1.5Chemaxon
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/MSsplash10-00di-0000900000-c916f188f432dfa4b7f2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0003900000-12c7ed2ed88924862524
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00gi-0008900000-1cd353d2c6dcb3f9488a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00c0-0009600000-a897f13aba6783b0ad92
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00o3-1039300000-edb50e0a94ab462dbdbb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00w9-0019100000-efc840d574d38ef1d604
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]-214.66142
predicted
DeepCCS 1.0 (2019)
[M+H]+217.5749
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.89235
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Genome polyprotein
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]
Details2. RNA-dependent RNA-polymerase
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. [Article]

Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52