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

ID: ALA4565832

PubChem CID: 155545209

Max Phase: Preclinical

Molecular Formula: C16H23N5O

Molecular Weight: 301.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1[C@@H]2CCC[C@H]1C[C@@H](Nc1nc3cc[nH]c3c(=O)n1C)C2

Standard InChI:  InChI=1S/C16H23N5O/c1-20-11-4-3-5-12(20)9-10(8-11)18-16-19-13-6-7-17-14(13)15(22)21(16)2/h6-7,10-12,17H,3-5,8-9H2,1-2H3,(H,18,19)/t10-,11+,12-

Standard InChI Key:  CWPFWNXQOCOJHE-ZSBIGDGJSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   38.0242   -3.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0242   -4.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7171   -4.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4100   -3.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7171   -2.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5020   -3.7640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5008   -4.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1965   -4.9801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8979   -4.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1947   -3.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8923   -3.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4905   -3.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.1636   -2.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3650   -2.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5946   -4.9769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.8052   -4.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.1963   -5.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1061   -4.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1122   -3.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7382   -3.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4130   -4.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8060   -2.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4027   -2.5589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.3089   -5.2498    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
 20 22  1  0
  4 23  1  1
  3 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4565832

   ---

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: 301.39

Molecular Weight (Monoisotopic): 301.1903

AlogP: 1.69

#Rotatable Bonds: 2

Polar Surface Area: 65.95

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 9.12

CX LogP: 0.99

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.89

Np Likeness Score: -0.22

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