US9034866, 442

ID: ALA3696722

PubChem CID: 89754866

Max Phase: Preclinical

Molecular Formula: C20H19N3O4S

Molecular Weight: 397.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COc2ccc(C#C[C@]3(O)CCN(C)C3=O)cc2-c2nc(C(N)=O)sc21

Standard InChI:  InChI=1S/C20H19N3O4S/c1-11-10-27-14-4-3-12(5-6-20(26)7-8-23(2)19(20)25)9-13(14)15-16(11)28-18(22-15)17(21)24/h3-4,9,11,26H,7-8,10H2,1-2H3,(H2,21,24)/t11-,20-/m0/s1

Standard InChI Key:  QGFVIJXZJDBZNA-YBTHPKLGSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    2.8552   -0.6517    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 O   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
   -2.4523    2.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2194    0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1198   -0.8265    0.0000 C   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
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135   -2.9844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -2.9844    0.0000 S   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
    0.0031   -5.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -5.9628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0350   -5.9661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6535   -0.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0877   -0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5218   -1.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3999   -0.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5218   -2.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2925   -3.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7545   -3.1538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6590   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8875   -1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9061   -1.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
 15 11  2  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19 20  3  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 21  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696722

   (4S)-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl]-4-methyl-4,5-dihydro-[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: 397.46

Molecular Weight (Monoisotopic): 397.1096

AlogP: 1.35

#Rotatable Bonds: 1

Polar Surface Area: 105.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.11

CX Basic pKa: ┄

CX LogP: 1.27

CX LogD: 1.27

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -0.09

References

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

Source

Source(1):

• BindingDB Database