US8524716, 29

ID: ALA3651545

PubChem CID: 42636960

Max Phase: Preclinical

Molecular Formula: C27H32N4O5S

Molecular Weight: 524.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C/C=C\CCNC(=O)Cn2c(-c3ccoc3)c(C3CCCCC3)c3ccc(cc32)C(=O)NS1(=O)=O

Standard InChI:  InChI=1S/C27H32N4O5S/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/h3,7,10-12,15-16,18-19H,2,4-6,8-9,13-14,17H2,1H3,(H,28,32)(H,29,33)/b7-3-

Standard InChI Key:  MLAQXRRWSYYBIG-CLTKARDFSA-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  2  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:

   

   ALA3651545

   (7Z)-18-cyclohexyl-19-(furan-3-yl)-10-methyl-11,11-dioxo-11lambda6-thia-1,4,10,12-tetrazatricyclo[12.5.2.017,20]henicosa-7,14(21),15,17(20),18-pentaene-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: 524.64

Molecular Weight (Monoisotopic): 524.2093

AlogP: 3.93

#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: 4.15

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.49

Np Likeness Score: 0.10

References

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

Source

Source(1):

• BindingDB Database