US8524716, 1

ID: ALA3651546

PubChem CID: 44129185

Max Phase: Preclinical

Molecular Formula: C27H31N3O3

Molecular Weight: 445.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Cn2c(-c3ccoc3)c(C3CCCCC3)c3ccc(cc32)C(=O)NCC/C=C\CCN1

Standard InChI:  InChI=1S/C27H31N3O3/c31-24-17-30-23-16-20(27(32)29-14-7-2-1-6-13-28-24)10-11-22(23)25(19-8-4-3-5-9-19)26(30)21-12-15-33-18-21/h1-2,10-12,15-16,18-19H,3-9,13-14,17H2,(H,28,31)(H,29,32)/b2-1-

Standard InChI Key:  FTPUPIQUARNDAE-UPHRSURJSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    3.5725    3.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807    2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    5.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    5.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    5.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    6.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097    7.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4714    7.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148    5.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268    7.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936    8.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9150    9.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   10.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4084    8.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870    7.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185    4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824    4.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5371    2.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    1.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808    2.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672    3.2954    0.0000 C   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
   -4.7810   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1240   -1.8037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203   -2.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1203   -2.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1240   -1.8036    0.0000 C   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
    3.4307    1.1147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
 11 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  4  1  0
 23 18  1  0
 21 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3651546

   (7Z)-17-cyclohexyl-18-(furan-3-yl)-1,4,11-triazatricyclo[11.5.2.016,19]icosa-7,13(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: 445.56

Molecular Weight (Monoisotopic): 445.2365

AlogP: 5.15

#Rotatable Bonds: 2

Polar Surface Area: 76.27

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 4.02

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: 0.26

References

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

Source

Source(1):

• BindingDB Database