3-Methyl-2-{[(1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-yl]-amino}-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

ID: ALA4541223

Max Phase: Preclinical

Molecular Formula: C15H21N5O

Molecular Weight: 287.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(N[C@@H]2C[C@H]3CCC[C@@H](C2)N3)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C15H21N5O/c1-20-14(21)13-12(5-6-16-13)19-15(20)18-11-7-9-3-2-4-10(8-11)17-9/h5-6,9-11,16-17H,2-4,7-8H2,1H3,(H,18,19)/t9-,10+,11-

Standard InChI Key:  YVISJQDBWVTOIL-JGPRNRPPSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   27.5728  -11.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5728  -11.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2829  -12.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9928  -11.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2829  -10.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1447  -11.5468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1435  -12.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8564  -12.7919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5750  -12.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8546  -11.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5693  -11.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1840  -10.9975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8508  -10.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0302  -10.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2930  -12.7887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4266  -12.7910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8562  -13.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7103  -12.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7165  -11.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3125  -11.5310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9960  -12.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9855  -10.3087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.6933  -12.9429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
  4  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 10  6  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  9 15  2  0
  7 16  1  0
  8 17  1  0
 18 16  1  6
 18 19  1  0
 18 21  1  0
 19  4  1  0
  4 20  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  6
  3 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4541223

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 287.37

Molecular Weight (Monoisotopic): 287.1746

AlogP: 1.35

#Rotatable Bonds: 2

Polar Surface Area: 74.74

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 9.97

CX LogP: 0.61

CX LogD: -1.95

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.78

Np Likeness Score: 0.10

References

1. Huang L, Li H, Li L, Niu L, Seupel R, Wu C, Cheng W, Chen C, Ding B, Brennan PE, Yang S..  (2019)  Discovery of Pyrrolo[3,2- d]pyrimidin-4-one Derivatives as a New Class of Potent and Cell-Active Inhibitors of P300/CBP-Associated Factor Bromodomain.,  62  (9): [PMID:30998845] [10.1021/acs.jmedchem.9b00096]

Source

Source(1):

• Scientific Literature