(1R,18R,20R,24S,27S)-24-cyclohexyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropane)sulfonyl]carbamoyl}cyclopropyl]-11-[(1-methylpiperidin-4-yl)oxy]-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: ALA3120493

Chembl Id: CHEMBL3120493

PubChem CID: 76314380

Max Phase: Preclinical

Molecular Formula: C47H64N6O9S

Molecular Weight: 889.13

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

Standard InChI:  InChI=1S/C47H64N6O9S/c1-4-31-27-47(31,44(56)51-63(58,59)46(2)21-22-46)50-41(54)37-26-33-28-53(37)43(55)39(29-13-7-5-8-14-29)49-45(57)62-38-25-30(38)15-9-6-10-17-35-40(60-32-19-23-52(3)24-20-32)34-16-11-12-18-36(34)48-42(35)61-33/h4,11-12,16,18,29-33,37-39H,1,5-10,13-15,17,19-28H2,2-3H3,(H,49,57)(H,50,54)(H,51,56)/t30-,31-,33-,37+,38-,39+,47-/m1/s1

Standard InChI Key:  BQXGLEULMMMZCS-UEFLQECUSA-N

Alternative Forms

1. Parent:

   

   ALA3120493

   (1R,18R,20R,24S,27S)-24-cyclohexyl-N-[(1R,2S)-2-ethenyl-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-11-(1-methylpiperidin-4-yl)oxy-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-pentaene-27-carboxa

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: 889.13

Molecular Weight (Monoisotopic): 888.4455

AlogP: 5.30

#Rotatable Bonds: 9

Polar Surface Area: 185.57

Molecular Species: ZWITTERION

HBA: 11

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.55

CX Basic pKa: 8.63

CX LogP: 4.00

CX LogD: 4.04

Aromatic Rings: 2

Heavy Atoms: 63

QED Weighted: 0.28

Np Likeness Score: 0.45

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