(1R,18R,20R,24S,27S)-24-cyclohexyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropane)sulfonyl]carbamoyl}cyclopropyl]-11-[3-(3-fluoroazetidin-1-yl)propoxy]-22,25-dioxo-2,21-dioxa-4,23,26-triazapentacyclo[24.2.1.0^{3,12}.0^{5,10}.0^{18,20}]nonacosa-3,5,7,9,11-pentaene-27-carboxamide

ID: ALA3120489

Chembl Id: CHEMBL3120489

PubChem CID: 76314379

Max Phase: Preclinical

Molecular Formula: C47H63FN6O9S

Molecular Weight: 907.12

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C1CCCCC1)NC(=O)O[C@@H]1C[C@H]1CCCCCc1c(nc3ccccc3c1OCCCN1CC(F)C1)O2)C(=O)NS(=O)(=O)C1(C)CC1

Standard InChI:  InChI=1S/C47H63FN6O9S/c1-3-31-25-47(31,44(57)52-64(59,60)46(2)19-20-46)51-41(55)37-24-33-28-54(37)43(56)39(29-13-6-4-7-14-29)50-45(58)63-38-23-30(38)15-8-5-9-17-35-40(61-22-12-21-53-26-32(48)27-53)34-16-10-11-18-36(34)49-42(35)62-33/h3,10-11,16,18,29-33,37-39H,1,4-9,12-15,17,19-28H2,2H3,(H,50,58)(H,51,55)(H,52,57)/t30-,31-,33-,37+,38-,39+,47-/m1/s1

Standard InChI Key:  LDQLVMJOLFWNSH-UEFLQECUSA-N

Associated Targets(non-human)

NS3 NS3 protease (146 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 907.12Molecular Weight (Monoisotopic): 906.4361AlogP: 5.25#Rotatable Bonds: 12
Polar Surface Area: 185.57Molecular Species: ACIDHBA: 11HBD: 3
#RO5 Violations: 3HBA (Lipinski): 15HBD (Lipinski): 3#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.55CX Basic pKa: 5.54CX LogP: 4.28CX LogD: 4.54
Aromatic Rings: 2Heavy Atoms: 64QED Weighted: 0.19Np Likeness Score: 0.31

References

1. Shah U, Jayne C, Chackalamannil S, Velázquez F, Guo Z, Buevich A, Howe JA, Chase R, Soriano A, Agrawal S, Rudd MT, McCauley JA, Liverton NJ, Romano J, Bush K, Coleman PJ, Grisé-Bard C, Brochu MC, Charron S, Aulakh V, Bachand B, Beaulieu P, Zaghdane H, Bhat S, Han Y, Vacca JP, Davies IW, Weber AE, Venkatraman S..  (2014)  Novel Quinoline-Based P2-P4 Macrocyclic Derivatives As Pan-Genotypic HCV NS3/4a Protease Inhibitors.,  (3): [PMID:24900818] [10.1021/ml400466p]

Source