NAV

N-[(2R,3S)-1-((2S)-2-{[(CYCLOPENTYLAMINO)CARBONYL]AMINO}-3-METHYLBUTANOYL)-2-(1-FORMYL-1-CYCLOBUTYL)PYRROLIDINYL]CYCLOPROPANECARBOXAMIDE

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
3D
Similar Structures
Weight
Average: 446.5829
Monoisotopic: 446.289305724
Chemical Formula
C24H38N4O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot Available
UNS3 proteaseNot 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-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
PubChem Compound
5287977
PubChem Substance
99444053
ChemSpider
4450228
ZINC
ZINC000033821260
PDBe Ligand
CPX
PDB Entries
1rtl

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 Solubility0.352 mg/mLALOGPS
logP1.77ALOGPS
logP1.46Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.66Chemaxon
pKa (Strongest Basic)-0.57Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area107.61 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity119.3 m3·mol-1Chemaxon
Polarizability49.2 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9762
Blood Brain Barrier-0.6402
Caco-2 permeable-0.6438
P-glycoprotein substrateSubstrate0.7033
P-glycoprotein inhibitor INon-inhibitor0.5695
P-glycoprotein inhibitor IINon-inhibitor0.8013
Renal organic cation transporterNon-inhibitor0.8965
CYP450 2C9 substrateNon-substrate0.7374
CYP450 2D6 substrateNon-substrate0.8058
CYP450 3A4 substrateSubstrate0.5305
CYP450 1A2 substrateNon-inhibitor0.8754
CYP450 2C9 inhibitorNon-inhibitor0.7835
CYP450 2D6 inhibitorNon-inhibitor0.9138
CYP450 2C19 inhibitorNon-inhibitor0.6708
CYP450 3A4 inhibitorNon-inhibitor0.815
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8792
Ames testNon AMES toxic0.6336
CarcinogenicityNon-carcinogens0.85
BiodegradationReady biodegradable0.6499
Rat acute toxicity2.3639 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9877
hERG inhibition (predictor II)Non-inhibitor0.7919
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/MSsplash10-000j-3129500000-b2717aab7043f580dd57
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-2029300000-eedd841854d321250edf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-3059200000-1526d7857e583c403714
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2189100000-290be5c6eef0f79763a1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-9503300000-ee4ceb22645a6c20d365
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gbd-4359400000-08f4abadb8cdb74a39ae
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]-206.00044
predicted
DeepCCS 1.0 (2019)
[M+H]+208.34099
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.00978
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Genome polyprotein
Kind
Protein
Organism
Not Available
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
P26664
Uniprot Name
Genome polyprotein
Molecular Weight
327198.77 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. NS3 protease
Kind
Protein
Organism
Hepatitis C Virus
Pharmacological action
Unknown
General Function
Serine-type peptidase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q91RS4
Uniprot Name
NS3 protease
Molecular Weight
19113.77 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 21:23 / Updated at June 12, 2020 16:52