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

ID: ALA4525423

PubChem CID: 155543203

Max Phase: Preclinical

Molecular Formula: C20H25N5O2

Molecular Weight: 367.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(N[C@@H]2C[C@H](c3ccccc3)CN(CCO)C2)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C20H25N5O2/c1-24-19(27)18-17(7-8-21-18)23-20(24)22-16-11-15(12-25(13-16)9-10-26)14-5-3-2-4-6-14/h2-8,15-16,21,26H,9-13H2,1H3,(H,22,23)/t15-,16+/m0/s1

Standard InChI Key:  MVNRAHCCLWOKDP-JKSUJKDBSA-N

Molfile:  

 
     RDKit          2D

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   38.3997   -3.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3997   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1050   -5.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8103   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8103   -3.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1050   -3.5659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5174   -5.2055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.2257   -4.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9312   -5.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.6390   -4.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2236   -3.9832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9285   -3.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6365   -3.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2468   -3.4394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.9159   -2.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1012   -2.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3469   -5.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9290   -6.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6926   -5.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9850   -4.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2784   -5.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2791   -6.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9924   -6.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6961   -6.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1050   -2.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8127   -2.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8127   -1.5229    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
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525423

   ---

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: 367.45

Molecular Weight (Monoisotopic): 367.2008

AlogP: 1.52

#Rotatable Bonds: 5

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: 12.00

CX Basic pKa: 7.75

CX LogP: 1.29

CX LogD: 0.75

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.60

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