(2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-4-(7-methoxy-2-phenylquinolin-4-yloxy)pyrrolidine-2-carboxamide

ID: ALA4224849

Chembl Id: CHEMBL4224849

PubChem CID: 5277161

Max Phase: Preclinical

Molecular Formula: C41H52N6O8S

Molecular Weight: 788.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2cc(-c3ccccc3)nc3cc(OC)ccc23)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1

Standard InChI:  InChI=1S/C41H52N6O8S/c1-9-25-22-41(25,37(50)46-56(52,53)28-16-17-28)44-35(48)32-20-27(23-47(32)36(49)34(39(2,3)4)43-38(51)45-40(5,6)7)55-33-21-30(24-13-11-10-12-14-24)42-31-19-26(54-8)15-18-29(31)33/h9-15,18-19,21,25,27-28,32,34H,1,16-17,20,22-23H2,2-8H3,(H,44,48)(H,46,50)(H2,43,45,51)/t25-,27-,32+,34-,41-/m1/s1

Standard InChI Key:  TYXDPFPMQGEZRQ-LMPQEXDPSA-N

Alternative Forms

1. Parent:

   

   ALA4224849

   (2S,4R)-1-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethyl-butanoyl]-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]-4-[(7-methoxy-2-phenyl-4-quinolyl)oxy]pyrrolidine-2-carboxamide

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: 788.97

Molecular Weight (Monoisotopic): 788.3567

AlogP: 4.44

#Rotatable Bonds: 12

Polar Surface Area: 185.13

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.76

CX Basic pKa: 5.60

CX LogP: 2.49

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 56

QED Weighted: 0.19

Np Likeness Score: -0.25

References

1. Venables BL, Sin N, Wang AX, Sun LQ, Tu Y, Hernandez D, Sheaffer A, Lee M, Dunaj C, Zhai G, Barry D, Friborg J, Yu F, Knipe J, Sandquist J, Falk P, Parker D, Good AC, Rajamani R, McPhee F, Meanwell NA, Scola PM..  (2018)  P3-P4 ureas and reverse carbamates as potent HCV NS3 protease inhibitors: Effective transposition of the P4 hydrogen bond donor.,  28  (10): [PMID:29650290] [10.1016/j.bmcl.2018.04.009]

Source

Source(1):

• Scientific Literature