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

ID: ALA4543497

PubChem CID: 155510571

Max Phase: Preclinical

Molecular Formula: C25H27N5O2

Molecular Weight: 429.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@H](c2ccc(Oc3ccccc3)cc2)C1

Standard InChI:  InChI=1S/C25H27N5O2/c1-29-15-18(17-8-10-21(11-9-17)32-20-6-4-3-5-7-20)14-19(16-29)27-25-28-22-12-13-26-23(22)24(31)30(25)2/h3-13,18-19,26H,14-16H2,1-2H3,(H,27,28)/t18-,19+/m0/s1

Standard InChI Key:  GVHCILCLTWXBGA-RBUKOAKNSA-N

Molfile:  

 
     RDKit          2D

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   32.8858   -3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8858   -4.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5952   -4.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.0117   -4.8670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7241   -4.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4337   -4.8700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1457   -4.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7220   -3.6365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4311   -3.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1432   -3.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7575   -3.0927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4225   -2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6038   -2.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8577   -4.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4316   -5.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1745   -4.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4627   -4.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7520   -4.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7527   -5.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4701   -6.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1780   -5.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5952   -2.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0420   -6.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3291   -5.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3305   -4.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6225   -4.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9108   -4.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9158   -5.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6285   -6.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  9 10  1  0
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 12 11  1  0
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 12 13  2  0
 13 14  1  0
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 15 16  2  0
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  9 18  1  0
  2 19  1  6
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 22 23  1  0
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 24 19  1  0
  6 25  1  0
 22 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:

   

   ALA4543497

   ---

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: 429.52

Molecular Weight (Monoisotopic): 429.2165

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 75.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 7.72

CX LogP: 3.48

CX LogD: 2.97

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.35

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