Isobutyl ((2R,6S,13aS,14aR,16aS,Z)-9'-methoxy-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-5'-(trifluoromethyl)-1',2',3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydro-1Hspiro[cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-2,3'-pyrano[2,3-c]quinolin]-6-yl)carbamate

ID: ALA3785323

Chembl Id: CHEMBL3785323

PubChem CID: 90060065

Max Phase: Preclinical

Molecular Formula: C40H50F3N5O9S

Molecular Weight: 833.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2nc(C(F)(F)F)c3c(c2c1)CC[C@]1(C[C@H]2C(=O)N[C@]4(C(=O)NS(=O)(=O)C5(C)CC5)C[C@H]4/C=C\CCCCC[C@H](NC(=O)OCC(C)C)C(=O)N2C1)O3

Standard InChI:  InChI=1S/C40H50F3N5O9S/c1-23(2)21-56-36(52)45-29-11-9-7-5-6-8-10-24-19-39(24,35(51)47-58(53,54)37(3)16-17-37)46-33(49)30-20-38(22-48(30)34(29)50)15-14-26-27-18-25(55-4)12-13-28(27)44-32(31(26)57-38)40(41,42)43/h8,10,12-13,18,23-24,29-30H,5-7,9,11,14-17,19-22H2,1-4H3,(H,45,52)(H,46,49)(H,47,51)/b10-8-/t24-,29+,30+,38-,39-/m1/s1

Standard InChI Key:  GBJKXZJNFVRHCK-XPTVTBSVSA-N

Alternative Forms

1. Parent:

   

   ALA3785323

   2-methylpropyl N-[(1'S,3R,4'R,6'S,7'Z,14'S)-9-methoxy-4'-[(1-methylcyclopropyl)sulfonylcarbamoyl]-2',15'-dioxo-5-(trifluoromethyl)spiro[1,2-dihydropyrano[2,3-c]quinoline-3,18'-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene]-14'-yl]carbamate

2. Alternative Forms:

   

   ALA3785323

   ---

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: 833.93

Molecular Weight (Monoisotopic): 833.3281

AlogP: 5.07

#Rotatable Bonds: 7

Polar Surface Area: 182.33

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.74

CX Basic pKa: 1.40

CX LogP: 5.01

CX LogD: 4.06

Aromatic Rings: 2

Heavy Atoms: 58

QED Weighted: 0.32

Np Likeness Score: 0.12

References

1. Neelamkavil SF, Agrawal S, Bara T, Bennett C, Bhat S, Biswas D, Brockunier L, Buist N, Burnette D, Cartwright M, Chackalamannil S, Chase R, Chelliah M, Chen A, Clasby M, Colandrea VJ, Davies IW, Eagen K, Guo Z, Han Y, Howe J, Jayne C, Josien H, Kargman S, Marcantonio K, Miao S, Miller R, Nolting A, Pinto P, Rajagopalan M, Ruck RT, Shah U, Soriano A, Sperbeck D, Velazquez F, Wu J, Xia Y, Venkatraman S..  (2016)  Discovery of MK-8831, A Novel Spiro-Proline Macrocycle as a Pan-Genotypic HCV-NS3/4a Protease Inhibitor.,  7  (1): [PMID:26819676] [10.1021/acsmedchemlett.5b00425]

2. Velázquez F, Chelliah M, Clasby M, Guo Z, Howe J, Miller R, Neelamkavil S, Shah U, Soriano A, Xia Y, Venkatraman S, Chackalamannil S, Davies IW..  (2016)  Design and Synthesis of P2-P4 Macrocycles Containing a Unique Spirocyclic Proline: A New Class of HCV NS3/4A Inhibitors.,  7  (12): [PMID:27994759] [10.1021/acsmedchemlett.6b00321]

Source

Source(1):

• Scientific Literature