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

ID: ALA4570924

PubChem CID: 155562459

Max Phase: Preclinical

Molecular Formula: C19H23N5O2

Molecular Weight: 353.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@H](c2ccc(O)cc2)C1

Standard InChI:  InChI=1S/C19H23N5O2/c1-23-10-13(12-3-5-15(25)6-4-12)9-14(11-23)21-19-22-16-7-8-20-17(16)18(26)24(19)2/h3-8,13-14,20,25H,9-11H2,1-2H3,(H,21,22)/t13-,14+/m0/s1

Standard InChI Key:  BXMGYRODWDXVQJ-UONOGXRCSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.4397   -3.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4397   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1491   -5.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -3.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1491   -3.4834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5656   -5.1312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2780   -4.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9876   -5.1341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6996   -4.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2760   -3.9007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9850   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6971   -3.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3115   -3.3568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9765   -2.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1577   -2.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4117   -5.1354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9855   -5.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7284   -5.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -4.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059   -5.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -5.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0241   -6.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7319   -5.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1491   -2.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960   -6.3641    0.0000 O   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
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570924

   ---

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: 353.43

Molecular Weight (Monoisotopic): 353.1852

AlogP: 1.87

#Rotatable Bonds: 3

Polar Surface Area: 86.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.19

CX Basic pKa: 7.77

CX LogP: 1.68

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -0.03

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