17-Cyclohexyl-18-(4-methoxy-phenyl)-9-methyl-10,10-dioxo-10lambda*6*-thia-1,4,9,11-tetraaza-tricyclo[11.5.2.0*16,19*]icosa-13,15,17,19-tetraene-3,12-dione

ID: ALA2042418

PubChem CID: 59549009

Max Phase: Preclinical

Molecular Formula: C29H36N4O5S

Molecular Weight: 552.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c(C3CCCCC3)c3ccc4cc3n2CC(=O)NCCCCN(C)S(=O)(=O)NC4=O)cc1

Standard InChI:  InChI=1S/C29H36N4O5S/c1-32-17-7-6-16-30-26(34)19-33-25-18-22(29(35)31-39(32,36)37)12-15-24(25)27(20-8-4-3-5-9-20)28(33)21-10-13-23(38-2)14-11-21/h10-15,18,20H,3-9,16-17,19H2,1-2H3,(H,30,34)(H,31,35)

Standard InChI Key:  YOLCBIVXUSHZAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.9175    6.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    6.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1203   -2.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1203   -2.9184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257   -3.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1240   -1.8036    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -3.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301   -1.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -0.3771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307    1.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720    1.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  6  9  1  0
  9 10  2  0
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 12 13  1  0
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 15 16  1  0
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 18 19  1  0
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 20 21  1  0
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 22 17  1  0
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 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 34 36  2  0
 34 37  1  0
 37 38  1  0
 38 20  1  0
 38 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2042418

   17-Cyclohexyl-18-(4-methoxyphenyl)-9-methyl-10,10-dioxo-10lambda6-thia-1,4,9,11-tetrazatricyclo[11.5.2.016,19]icosa-13(20),14,16(19),17-tetraene-3,12-dione

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: 552.70

Molecular Weight (Monoisotopic): 552.2406

AlogP: 4.18

#Rotatable Bonds: 3

Polar Surface Area: 109.74

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.16

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 2.51

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.51

Np Likeness Score: -0.21

References

1. McGowan D, Vendeville S, Lin TI, Tahri A, Hu L, Cummings MD, Amssoms K, Berke JM, Canard M, Cleiren E, Dehertogh P, Last S, Fransen E, Van Der Helm E, Van den Steen I, Vijgen L, Rouan MC, Fanning G, Nyanguile O, Van Emelen K, Simmen K, Raboisson P..  (2012)  Finger-loop inhibitors of the HCV NS5b polymerase. Part 1: Discovery and optimization of novel 1,6- and 2,6-macrocyclic indole series.,  22  (13): [PMID:22542193] [10.1016/j.bmcl.2012.03.097]

2.  (2013)  Macrocyclic indoles as hepatitis C virus inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database