3-Methyl-2-{[(3R,5R)-5-phenyl-1-(2-phenylethyl)-piperidin-3-yl]amino}-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one

ID: ALA4528565

PubChem CID: 155544937

Max Phase: Preclinical

Molecular Formula: C26H29N5O

Molecular Weight: 427.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(N[C@@H]2C[C@H](c3ccccc3)CN(CCc3ccccc3)C2)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C26H29N5O/c1-30-25(32)24-23(12-14-27-24)29-26(30)28-22-16-21(20-10-6-3-7-11-20)17-31(18-22)15-13-19-8-4-2-5-9-19/h2-12,14,21-22,27H,13,15-18H2,1H3,(H,28,29)/t21-,22+/m0/s1

Standard InChI Key:  CYAQNRXNBFHDQR-FCHUYYIVSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    5.4562  -13.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4562  -14.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1615  -14.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1615  -13.1328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5739  -14.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2822  -14.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9876  -14.7753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6955  -14.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2801  -13.5501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9850  -13.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6930  -13.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3032  -13.0063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9723  -12.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1577  -12.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4034  -14.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9855  -15.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7491  -14.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414  -14.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348  -14.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356  -15.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488  -15.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7525  -15.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1615  -12.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692  -11.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692  -11.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5799  -10.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5803   -9.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -9.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1620   -9.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1651  -10.6866    0.0000 C   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
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 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
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4528565

   ---

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: 427.55

Molecular Weight (Monoisotopic): 427.2372

AlogP: 3.77

#Rotatable Bonds: 6

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: 8.84

CX LogP: 3.99

CX LogD: 2.51

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.49

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