tert-butyl 4-{[(1R,18R,20R,24S,27S)-24-cyclohexyl-27-{[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropane)sulfonyl]carbamoyl}cyclopropyl]carbamoyl}-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-pentaen-11-yl]oxy}piperidine-1-carboxylate

ID: ALA3120474

Chembl Id: CHEMBL3120474

PubChem CID: 76325272

Max Phase: Preclinical

Molecular Formula: C51H70N6O11S

Molecular Weight: 975.22

Molecule Type: Small molecule

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(nc3ccccc3c1OC1CCN(C(=O)OC(C)(C)C)CC1)O2)C(=O)NS(=O)(=O)C1(C)CC1

Standard InChI:  InChI=1S/C51H70N6O11S/c1-6-33-29-51(33,46(60)55-69(63,64)50(5)23-24-50)54-43(58)39-28-35-30-57(39)45(59)41(31-15-9-7-10-16-31)53-47(61)67-40-27-32(40)17-11-8-12-19-37-42(36-18-13-14-20-38(36)52-44(37)66-35)65-34-21-25-56(26-22-34)48(62)68-49(2,3)4/h6,13-14,18,20,31-35,39-41H,1,7-12,15-17,19,21-30H2,2-5H3,(H,53,61)(H,54,58)(H,55,60)/t32-,33-,35-,39+,40-,41+,51-/m1/s1

Standard InChI Key:  VIEYATVGDANFPT-GRZCADDISA-N

Alternative Forms

1. Parent:

   

   ALA3120474

   tert-butyl 4-[[(1R,18R,20R,24S,27S)-24-cyclohexyl-27-[[(1R,2S)-2-ethenyl-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]carbamoyl]-22,25-dioxo-2,21-dioxa-4,23,26-triazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5,7,9,11-pentaen-11-yl]oxy]piper

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 975.22

Molecular Weight (Monoisotopic): 974.4823

AlogP: 6.60

#Rotatable Bonds: 9

Polar Surface Area: 211.87

Molecular Species: ACID

HBA: 12

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.58

CX Basic pKa: 4.25

CX LogP: 5.54

CX LogD: 5.31

Aromatic Rings: 2

Heavy Atoms: 69

QED Weighted: 0.23

Np Likeness Score: 0.27

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.,  5  (3): [PMID:24900818] [10.1021/ml400466p]

Source

Source(1):

• Scientific Literature