US8524716, 23

ID: ALA3651544

PubChem CID: 59549092

Max Phase: Preclinical

Molecular Formula: C29H33ClN4O4S

Molecular Weight: 569.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C/C=C\CN(C)S(=O)(=O)NC(=O)c2ccc3c(C4CCCCC4)c(-c4ccc(Cl)cc4)n(c3c2)CC1=O

Standard InChI:  InChI=1S/C29H33ClN4O4S/c1-32-16-6-7-17-33(2)39(37,38)31-29(36)22-12-15-24-25(18-22)34(19-26(32)35)28(21-10-13-23(30)14-11-21)27(24)20-8-4-3-5-9-20/h6-7,10-15,18,20H,3-5,8-9,16-17,19H2,1-2H3,(H,31,36)/b7-6-

Standard InChI Key:  UEDANJNSPPDNGK-SREVYHEPSA-N

Molfile:  

     RDKit          2D

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    1.4672    3.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5875   -0.3771    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1870   -0.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8119    3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    2.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560    0.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9935    1.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962    2.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5578    1.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6800    1.6742    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3167   -0.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1240   -1.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -0.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5720    1.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7500   -3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  1  0
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 15 16  2  0
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 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
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 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 20  1  0
 19 26  2  0
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 27 28  2  0
 28 29  1  0
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 30 31  1  0
 30 32  1  0
 32 33  2  0
 33 27  1  0
 26 34  1  0
 34 35  1  0
 35 36  1  0
 36  2  1  0
 36 37  2  0
 34 38  1  0
 38 18  1  0
 38 39  2  0
 39 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3651544

   (6Z)-18-(4-chlorophenyl)-17-cyclohexyl-4,9-dimethyl-10,10-dioxo-10lambda6-thia-1,4,9,11-tetrazatricyclo[11.5.2.016,19]icosa-6,13(20),14,16(19),17-pentaene-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: 569.13

Molecular Weight (Monoisotopic): 568.1911

AlogP: 4.94

#Rotatable Bonds: 2

Polar Surface Area: 91.72

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.44

Np Likeness Score: -0.30

References

1.  (2013)  Macrocyclic indoles as hepatitis C virus inhibitors, 

Source

Source(1):

• BindingDB Database