3-Methyl-2-{[(3S,5S)-1-methyl-5-phenylpiperidin-3-yl]-amino}-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

ID: ALA4584442

PubChem CID: 155566697

Max Phase: Preclinical

Molecular Formula: C19H23N5O

Molecular Weight: 337.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@@H](c2ccccc2)C1

Standard InChI:  InChI=1S/C19H23N5O/c1-23-11-14(13-6-4-3-5-7-13)10-15(12-23)21-19-22-16-8-9-20-17(16)18(25)24(19)2/h3-9,14-15,20H,10-12H2,1-2H3,(H,21,22)/t14-,15+/m1/s1

Standard InChI Key:  JRIBEBYKWORBGC-CABCVRRESA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   18.3813   -3.1821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3801   -4.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0882   -4.4188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8019   -4.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0864   -2.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7963   -3.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4069   -2.6364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0759   -1.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2608   -1.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5151   -4.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6680   -4.4179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0880   -5.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9564   -4.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9610   -3.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2536   -2.7701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5390   -3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5364   -3.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2484   -4.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8229   -4.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1167   -3.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4036   -4.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3997   -5.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1148   -5.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8250   -5.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2573   -1.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  5  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  2  0
  2 11  1  0
  3 12  1  0
 13 11  1  1
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4584442

   ---

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: 337.43

Molecular Weight (Monoisotopic): 337.1903

AlogP: 2.16

#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: 7.90

CX LogP: 1.98

CX LogD: 1.32

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -0.31

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