2-{[(3R,5R)-5-(3-bromophenyl)-1-methylpiperidin-3-yl]-amino}-3-methyl-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

ID: ALA4545594

PubChem CID: 155553182

Max Phase: Preclinical

Molecular Formula: C19H22BrN5O

Molecular Weight: 416.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@H](c2cccc(Br)c2)C1

Standard InChI:  InChI=1S/C19H22BrN5O/c1-24-10-13(12-4-3-5-14(20)8-12)9-15(11-24)22-19-23-16-6-7-21-17(16)18(26)25(19)2/h3-8,13,15,21H,9-11H2,1-2H3,(H,22,23)/t13-,15+/m0/s1

Standard InChI Key:  UAQWSIGLPCUFJO-DZGCQCFKSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.8597  -12.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8597  -13.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5650  -13.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2703  -13.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2703  -12.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5650  -12.0721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9774  -13.7117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6857  -13.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3912  -13.7146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0990  -13.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6836  -12.4894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3885  -12.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0965  -12.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7068  -11.9456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3759  -11.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5612  -11.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8069  -13.7159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3890  -14.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1526  -13.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4450  -13.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7383  -13.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7391  -14.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4524  -14.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1561  -14.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5650  -11.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0302  -13.3039    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 11  8  2  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 10 17  2  0
  9 18  1  0
  2 19  1  6
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  6 25  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4545594

   ---

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: 416.32

Molecular Weight (Monoisotopic): 415.1008

AlogP: 2.92

#Rotatable Bonds: 3

Polar Surface Area: 65.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 6.82

CX LogP: 2.75

CX LogD: 2.65

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -0.46

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