US9034866, 460

ID: ALA3696731

PubChem CID: 86693531

Max Phase: Preclinical

Molecular Formula: C21H20N4O4

Molecular Weight: 392.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@@](O)(C#Cc2ccc3c(c2)-n2nc(C(N)=O)cc2C2(CC2)CO3)C1=O

Standard InChI:  InChI=1S/C21H20N4O4/c1-24-9-8-21(28,19(24)27)5-4-13-2-3-16-15(10-13)25-17(11-14(23-25)18(22)26)20(6-7-20)12-29-16/h2-3,10-11,28H,6-9,12H2,1H3,(H2,22,26)/t21-/m0/s1

Standard InChI Key:  XTLQTVSITXHZBU-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 29 33  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
   -2.5424    1.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    2.5670    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
   -3.0899   -0.9120    0.0000 C   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 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
    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
    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  0
 16 17  1  0
 17 15  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 22 23  1  0
 23 12  1  0
 23 24  2  0
 24  9  1  0
 20 25  1  0
 25 26  2  0
 25 27  1  0
  5 28  1  0
 28  2  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696731

   (R)-9-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-5H-spiro[benzo[b]pyrazolo[1,5-d][1,4]oxazepine-4,1'-cyclopropane]-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: 392.42

Molecular Weight (Monoisotopic): 392.1485

AlogP: 0.34

#Rotatable Bonds: 1

Polar Surface Area: 110.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: ┄

CX LogP: 0.38

CX LogD: 0.38

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.30

References

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

Source

Source(1):

• BindingDB Database