N-[(2R,3S)-1-((2S)-2-{[(CYCLOPENTYLAMINO)CARBONYL]AMINO}-3-METHYLBUTANOYL)-2-(1-FORMYL-1-CYCLOBUTYL)PYRROLIDINYL]CYCLOPROPANECARBOXAMIDE
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Identification
- Generic Name
- N-[(2R,3S)-1-((2S)-2-{[(CYCLOPENTYLAMINO)CARBONYL]AMINO}-3-METHYLBUTANOYL)-2-(1-FORMYL-1-CYCLOBUTYL)PYRROLIDINYL]CYCLOPROPANECARBOXAMIDE
- DrugBank Accession Number
- DB07582
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 446.5829
Monoisotopic: 446.289305724 - Chemical Formula
- C24H38N4O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGenome polyprotein Not Available UNS3 protease 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-carbamoyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl 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-carbamoyl-alpha amino acids and derivatives
- Alternative Parents
- Valine and derivatives / Alpha amino acid amides / N-acylpyrrolidines / Cyclopropanecarboxylic acids and derivatives / Tertiary carboxylic acid amides / Ureas / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 3 more
- Substituents
- Aldehyde / Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Azacycle / Carbonic acid derivative / Carbonyl group / Carboxamide group / Cyclopropanecarboxylic acid or derivatives / Hydrocarbon derivative / N-acylpyrrolidine show 13 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- ureas, monocarboxylic acid amide, N-acylpyrrolidine (CHEBI:41590)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- GCDRFILPPBOJLM-UFYCRDLUSA-N
- InChI
- InChI=1S/C24H38N4O4/c1-15(2)19(27-23(32)25-17-6-3-4-7-17)22(31)28-13-10-18(26-21(30)16-8-9-16)20(28)24(14-29)11-5-12-24/h14-20H,3-13H2,1-2H3,(H,26,30)(H2,25,27,32)/t18-,19-,20-/m0/s1
- IUPAC Name
- N-[(2R,3S)-1-[(2S)-2-[(cyclopentylcarbamoyl)amino]-3-methylbutanoyl]-2-(1-formylcyclobutyl)pyrrolidin-3-yl]cyclopropanecarboxamide
- SMILES
- [H][C@](NC(=O)NC1CCCC1)(C(C)C)C(=O)N1CC[C@]([H])(NC(=O)C2CC2)[C@@]1([H])C1(CCC1)C=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5287977
- PubChem Substance
- 99444053
- ChemSpider
- 4450228
- ZINC
- ZINC000033821260
- PDBe Ligand
- CPX
- PDB Entries
- 1rtl
Clinical Trials
- Clinical Trials
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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 0.352 mg/mL ALOGPS logP 1.77 ALOGPS logP 1.46 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 14.66 Chemaxon pKa (Strongest Basic) -0.57 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 107.61 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 119.3 m3·mol-1 Chemaxon Polarizability 49.2 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9762 Blood Brain Barrier - 0.6402 Caco-2 permeable - 0.6438 P-glycoprotein substrate Substrate 0.7033 P-glycoprotein inhibitor I Non-inhibitor 0.5695 P-glycoprotein inhibitor II Non-inhibitor 0.8013 Renal organic cation transporter Non-inhibitor 0.8965 CYP450 2C9 substrate Non-substrate 0.7374 CYP450 2D6 substrate Non-substrate 0.8058 CYP450 3A4 substrate Substrate 0.5305 CYP450 1A2 substrate Non-inhibitor 0.8754 CYP450 2C9 inhibitor Non-inhibitor 0.7835 CYP450 2D6 inhibitor Non-inhibitor 0.9138 CYP450 2C19 inhibitor Non-inhibitor 0.6708 CYP450 3A4 inhibitor Non-inhibitor 0.815 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8792 Ames test Non AMES toxic 0.6336 Carcinogenicity Non-carcinogens 0.85 Biodegradation Ready biodegradable 0.6499 Rat acute toxicity 2.3639 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9877 hERG inhibition (predictor II) Non-inhibitor 0.7919
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000j-3129500000-b2717aab7043f580dd57 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00lr-2029300000-eedd841854d321250edf Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-3059200000-1526d7857e583c403714 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-2189100000-290be5c6eef0f79763a1 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uxr-9503300000-ee4ceb22645a6c20d365 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0gbd-4359400000-08f4abadb8cdb74a39ae 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]- 206.00044 predictedDeepCCS 1.0 (2019) [M+H]+ 208.34099 predictedDeepCCS 1.0 (2019) [M+Na]+ 215.00978 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGenome polyprotein
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Unknown
- General Function
- Mature core protein Packages viral RNA to form a viral nucleocapsid, and promotes virion budding (Probable). Participates in the viral particle production as a result of its interaction with the non-structural protein 5A (By similarity). Binds RNA and may function as a RNA chaperone to induce the RNA structural rearrangements taking place during virus replication (By similarity). Modulates viral translation initiation by interacting with viral IRES and 40S ribosomal subunit (By similarity). Affects various cell signaling pathways, host immunity and lipid metabolism (Probable). Prevents the establishment of cellular antiviral state by blocking the interferon-alpha/beta (IFN-alpha/beta) and IFN-gamma signaling pathways and by blocking the formation of phosphorylated STAT1 and promoting ubiquitin-mediated proteasome-dependent degradation of STAT1 (By similarity). Activates STAT3 leading to cellular transformation (By similarity). Regulates the activity of cellular genes, including c-myc and c-fos (PubMed:8533458). May repress the promoter of p53, and sequester CREB3 and SP110 isoform 3/Sp110b in the cytoplasm (PubMed:9110985). Represses cell cycle negative regulating factor CDKN1A, thereby interrupting an important check point of normal cell cycle regulation (PubMed:9524287). Targets transcription factors involved in the regulation of inflammatory responses and in the immune response: suppresses TNF-induced NF-kappa-B activation, and activates AP-1 (PubMed:9811706). Binds to dendritic cells (DCs) via C1QR1, resulting in down-regulation of T-lymphocytes proliferation (By similarity). Alters lipid metabolism by interacting with hepatocellular proteins involved in lipid accumulation and storage (By similarity). Induces up-regulation of FAS promoter activity, and thereby contributes to the increased triglyceride accumulation in hepatocytes (steatosis) (By similarity).
- Specific Function
- ATP binding
- Gene Name
- Not Available
- Uniprot ID
- P26664
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 327198.77 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. DetailsNS3 protease
- Kind
- Protein
- Organism
- Hepatitis C Virus
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- metal ion binding
- Gene Name
- Not Available
- Uniprot ID
- Q91RS4
- Uniprot Name
- NS3 protease
- Molecular Weight
- 19113.77 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 21:23 / Updated at June 12, 2020 16:52