(2S,4S,5R)-2-ISOBUTYL-5-(2-THIENYL)-1-[4-(TRIFLUOROMETHYL)BENZOYL]PYRROLIDINE-2,4-DICARBOXYLIC ACID
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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
- Weight
- Average: 469.474
Monoisotopic: 469.117078124 - Chemical Formula
- C22H22F3NO5S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGenome polyprotein Not Available Hepatitis C virus genotype 1b (isolate BK) URNA-dependent RNA-polymerase Not Available Hepatitis 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 5275422
- PubChem Substance
- 99443671
- ChemSpider
- 4439526
- BindingDB
- 50162519
- ChEMBL
- CHEMBL180948
- ZINC
- ZINC000016052233
- PDBe Ligand
- 699
- PDB Entries
- 2jc0
Clinical Trials
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
Property Value Source Water Solubility 0.00317 mg/mL ALOGPS logP 3.51 ALOGPS logP 5.01 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 4.1 Chemaxon pKa (Strongest Basic) -1.5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 94.91 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 109.92 m3·mol-1 Chemaxon Polarizability 42.77 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.996 Blood Brain Barrier + 0.5059 Caco-2 permeable - 0.5898 P-glycoprotein substrate Non-substrate 0.6799 P-glycoprotein inhibitor I Non-inhibitor 0.8589 P-glycoprotein inhibitor II Non-inhibitor 0.5542 Renal organic cation transporter Non-inhibitor 0.9523 CYP450 2C9 substrate Non-substrate 0.7552 CYP450 2D6 substrate Non-substrate 0.8068 CYP450 3A4 substrate Substrate 0.5064 CYP450 1A2 substrate Non-inhibitor 0.8283 CYP450 2C9 inhibitor Non-inhibitor 0.7096 CYP450 2D6 inhibitor Non-inhibitor 0.9125 CYP450 2C19 inhibitor Non-inhibitor 0.5992 CYP450 3A4 inhibitor Non-inhibitor 0.9058 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7345 Ames test Non AMES toxic 0.7931 Carcinogenicity Non-carcinogens 0.7417 Biodegradation Not ready biodegradable 0.9953 Rat acute toxicity 2.4526 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9993 hERG inhibition (predictor II) Non-inhibitor 0.7973
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-c916f188f432dfa4b7f2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0003900000-12c7ed2ed88924862524 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00gi-0008900000-1cd353d2c6dcb3f9488a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00c0-0009600000-a897f13aba6783b0ad92 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00o3-1039300000-edb50e0a94ab462dbdbb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00w9-0019100000-efc840d574d38ef1d604 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 214.66142 predictedDeepCCS 1.0 (2019) [M+H]+ 217.5749 predictedDeepCCS 1.0 (2019) [M+Na]+ 224.89235 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGenome 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
- 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]
2. DetailsRNA-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
- 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