(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-(2-(4-cyclopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-6-(3,3-diethylureido)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide

ID: ALA2208398

PubChem CID: 46870068

Max Phase: Preclinical

Molecular Formula: C43H55N7O8S2

Molecular Weight: 862.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)N[C@H]1CCCCC/C=C\[C@@H]2C[C@@]2(C(=O)NS(=O)(=O)C2CC2)NC(=O)[C@@H]2C[C@@H](Oc3cc(-c4nc(C5CC5)cs4)nc4c(C)c(OC)ccc34)CN2C1=O

Standard InChI:  InChI=1S/C43H55N7O8S2/c1-5-49(6-2)42(54)46-31-13-11-9-7-8-10-12-27-22-43(27,41(53)48-60(55,56)29-16-17-29)47-38(51)34-20-28(23-50(34)40(31)52)58-36-21-32(39-45-33(24-59-39)26-14-15-26)44-37-25(3)35(57-4)19-18-30(36)37/h10,12,18-19,21,24,26-29,31,34H,5-9,11,13-17,20,22-23H2,1-4H3,(H,46,54)(H,47,51)(H,48,53)/b12-10-/t27-,28-,31+,34+,43-/m1/s1

Standard InChI Key:  OUHBFQUQWAGKAY-AHQRLGNQSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2208398

   (2R,6S,13aS,14aR,16aS,Z)-N-(cyclopropylsulfonyl)-2-(2-(4-cyclopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-6-(3,3-diethylureido)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentad

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: 862.09

Molecular Weight (Monoisotopic): 861.3554

AlogP: 5.32

#Rotatable Bonds: 11

Polar Surface Area: 189.23

Molecular Species: ACID

HBA: 11

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.77

CX Basic pKa: 1.59

CX LogP: 4.36

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 60

QED Weighted: 0.21

Np Likeness Score: -0.35

References

1. Li X, Liu Y, Zhang YK, Plattner JJ, Baker SJ, Bu W, Liu L, Zhou Y, Ding CZ, Zhang S, Kazmierski WM, Hamatake R, Duan M, Wright LL, Smith GK, Jarvest RL, Ji JJ, Cooper JP, Tallant MD, Crosby RM, Creech K, Wang A..  (2012)  Synthesis and antiviral activity of novel HCV NS3 protease inhibitors with P4 capping groups.,  22  (24): [PMID:23142614] [10.1016/j.bmcl.2012.10.075]

Source

Source(1):

• Scientific Literature