18-Cyclohexyl-19-furan-3-yl-10-methyl-11,11-dioxo-11lambda*6*-thia-1,4,10,12-tetraaza-tricyclo[12.5.2.0*17,20*]henicosa-14,16,18,20-tetraene-3,13-dione

ID: ALA2042441

PubChem CID: 44128275

Max Phase: Preclinical

Molecular Formula: C27H34N4O5S

Molecular Weight: 526.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCCCCNC(=O)Cn2c(-c3ccoc3)c(C3CCCCC3)c3ccc(cc32)C(=O)NS1(=O)=O

Standard InChI:  InChI=1S/C27H34N4O5S/c1-30-14-7-3-6-13-28-24(32)17-31-23-16-20(27(33)29-37(30,34)35)10-11-22(23)25(19-8-4-2-5-9-19)26(31)21-12-15-36-18-21/h10-12,15-16,18-19H,2-9,13-14,17H2,1H3,(H,28,32)(H,29,33)

Standard InChI Key:  OLRIZJFQQRRDDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
    3.5669    3.5669    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
    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 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
   -3.5517    1.4712    0.0000 C   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
   -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
   -2.2053   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6956   -5.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716   -4.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0804   -4.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7879   -6.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2983   -6.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871   -5.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -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
   -1.8379  -10.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -9.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2767   -8.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751   -5.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8885   -5.7933    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
    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 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437    2.6677    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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
 13 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 20  1  0
 19 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 12  1  0
 31 26  1  0
 29 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35  2  1  0
 35 36  2  0
 35 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2042441

   18-Cyclohexyl-19-(furan-3-yl)-10-methyl-11,11-dioxo-11lambda6-thia-1,4,10,12-tetrazatricyclo[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: 526.66

Molecular Weight (Monoisotopic): 526.2250

AlogP: 4.16

#Rotatable Bonds: 2

Polar Surface Area: 113.65

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: 3.19

CX LogD: 2.25

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.52

Np Likeness Score: -0.03

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