US9034866, 427

ID: ALA3696713

PubChem CID: 86693509

Max Phase: Preclinical

Molecular Formula: C23H21N5O2

Molecular Weight: 399.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(C(N)=O)nc2c1C1CC(C1)c1ccc(C#C[C@@](C)(O)c3ncccn3)cc1-2

Standard InChI:  InChI=1S/C23H21N5O2/c1-23(30,22-25-8-3-9-26-22)7-6-13-4-5-16-14-11-15(12-14)19-18(17(16)10-13)27-21(20(24)29)28(19)2/h3-5,8-10,14-15,30H,11-12H2,1-2H3,(H2,24,29)/t14?,15?,23-/m1/s1

Standard InChI Key:  AGGVOSCHXCTTHA-CKBDLISKSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  1  0  0  0  0  0999 V2000
    1.1551   -3.9330    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
    3.0226   -2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0899   -0.9120    0.0000 N   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
    2.5913    1.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278    4.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1116    3.2255    0.0000 C   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 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
    0.1165    0.0266    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
    3.7193    4.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9593    5.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1993    5.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1093    7.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2894    4.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5519    5.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6650    3.8100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0169    3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2557    4.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1426    5.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7908    6.1515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959   -3.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3124   -2.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -4.5291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 12  1  0
 14 16  1  0
 16  2  1  0
 16  5  2  0
  8 17  1  0
 17 18  3  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  3 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696713

   (R)-9-(3-hydroxy-3-(pyrimidin-2-yl)but-1-yn-1-yl)-3-methyl-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-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: 399.45

Molecular Weight (Monoisotopic): 399.1695

AlogP: 2.21

#Rotatable Bonds: 2

Polar Surface Area: 106.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.41

CX Basic pKa: 2.25

CX LogP: 2.09

CX LogD: 2.09

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -0.36

References

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

Source

Source(1):

• BindingDB Database