US9034866, 428

ID: ALA3696714

PubChem CID: 89754608

Max Phase: Preclinical

Molecular Formula: C20H19N3O4

Molecular Weight: 365.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CCC(O)(C#Cc3ccc4c(c3)-c3nc(C(N)=O)cn3CCO4)C1O2

Standard InChI:  InChI=1S/C20H19N3O4/c1-19-6-7-20(25,18(19)27-19)5-4-12-2-3-15-13(10-12)17-22-14(16(21)24)11-23(17)8-9-26-15/h2-3,10-11,18,25H,6-9H2,1H3,(H2,21,24)

Standard InChI Key:  AXBSFVMHABHIGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.2935   -8.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -9.5928    0.0000 C   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
   -1.6852   -0.3847    0.0000 N   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 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
    4.8672   -8.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8606  -10.3176    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  0
  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 18  2  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 20 21  1  0
 21 12  1  0
 21 22  2  0
 22  9  1  0
 18 23  1  0
 23 24  2  0
 23 25  1  0
  5 26  1  0
 26  2  1  0
 26 27  1  0
 27  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696714

   10-[2-(2-Hydroxy-5-methyl-6-oxabicyclo[3.1.0]hexan-2-yl)ethynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-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: 365.39

Molecular Weight (Monoisotopic): 365.1376

AlogP: 1.08

#Rotatable Bonds: 1

Polar Surface Area: 102.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.10

CX Basic pKa: 2.36

CX LogP: 1.29

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 0.32

References

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

Source

Source(1):

• BindingDB Database