US9034866, 458

ID: ALA3696729

PubChem CID: 89755413

Max Phase: Preclinical

Molecular Formula: C20H16F3N3O5S

Molecular Weight: 467.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@@](O)(C#Cc2ccc3c(c2)-c2nc(C(N)=O)sc2[C@@](O)(C(F)(F)F)CO3)C1=O

Standard InChI:  InChI=1S/C20H16F3N3O5S/c1-26-7-6-18(29,17(26)28)5-4-10-2-3-12-11(8-10)13-14(32-16(25-13)15(24)27)19(30,9-31-12)20(21,22)23/h2-3,8,29-30H,6-7,9H2,1H3,(H2,24,27)/t18-,19+/m0/s1

Standard InChI Key:  NBHMPSMAEPUDTP-RBUKOAKNSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  1  0  0  0  0  0999 V2000
    3.5635  -10.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -9.5928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425   -8.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -7.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272   -7.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6141   -7.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -5.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306   -4.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822   -3.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7175   -2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695   -0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358    2.2582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899   -0.9120    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0226   -2.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5767   -2.8095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920   -3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0115   -4.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3099   -2.9106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072    0.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8866   -0.6903    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244    0.0581    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453    1.2445    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8672   -8.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9983   -9.1659    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  6
  5  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 21 22  1  0
 22 12  1  0
 22 23  2  0
 23  9  1  0
 19 24  1  0
 24 25  2  0
 24 26  1  0
 15 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  5 31  1  0
 31  2  1  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696729

   (4S)-4-hydroxy-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl]-4-(trifluoromethyl)-5H-[1]benzoxepino[5,4-d][1,3]thiazole-2-carboxamide

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: 467.43

Molecular Weight (Monoisotopic): 467.0763

AlogP: 1.00

#Rotatable Bonds: 1

Polar Surface Area: 125.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.25

CX Basic pKa: ┄

CX LogP: 0.87

CX LogD: 0.86

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -0.33

References

1.  (2015)  Tricyclic compounds and methods of use therefor, 

Source

Source(1):

• BindingDB Database