18-Cyclohexyl-19-(4-methoxy-phenyl)-7-methyl-11,11-dioxo-11lambda*6*-thia-1,4,7,10,12-pentaaza-tricyclo[12.5.2.0*17,20*]henicosa-14,16,18,20-tetraene-3,13-dione

ID: ALA2042419

PubChem CID: 44128274

Max Phase: Preclinical

Molecular Formula: C29H37N5O5S

Molecular Weight: 567.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c(C3CCCCC3)c3ccc4cc3n2CC(=O)NCCN(C)CCNS(=O)(=O)NC4=O)cc1

Standard InChI:  InChI=1S/C29H37N5O5S/c1-33-16-14-30-26(35)19-34-25-18-22(29(36)32-40(37,38)31-15-17-33)10-13-24(25)27(20-6-4-3-5-7-20)28(34)21-8-11-23(39-2)12-9-21/h8-13,18,20,31H,3-7,14-17,19H2,1-2H3,(H,30,35)(H,32,36)

Standard InChI Key:  YZZRXBQQGYLYBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
   -8.8323    4.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1893    5.2320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6897    5.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8841    6.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    6.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6956    5.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4981    3.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9967    3.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054    4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1872    5.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800    7.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558    8.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    9.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   10.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4579    9.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    8.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750    5.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8885    5.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765    4.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184    2.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712    3.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4712    3.5517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184    2.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517    1.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6604    1.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517   -1.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184   -2.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4712   -3.5517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9304   -4.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -3.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -2.7184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -1.4712    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -2.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4628   -0.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    1.9304    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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 11  1  0
 10 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 22 23  1  0
 23  9  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  2  0
 35 38  1  0
 38 39  1  0
 39 20  1  0
 39 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2042419

   18-Cyclohexyl-19-(4-methoxyphenyl)-7-methyl-11,11-dioxo-11lambda6-thia-1,4,7,10,12-pentazatricyclo[12.5.2.017,20]henicosa-14(21),15,17(20),18-tetraene-3,13-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: 567.71

Molecular Weight (Monoisotopic): 567.2515

AlogP: 2.99

#Rotatable Bonds: 3

Polar Surface Area: 121.77

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.11

CX Basic pKa: 6.15

CX LogP: 1.39

CX LogD: 1.71

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.45

Np Likeness Score: -0.28

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