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

ID: ALA4537244

PubChem CID: 155548574

Max Phase: Preclinical

Molecular Formula: C22H27N5O

Molecular Weight: 377.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCCn1c(N[C@@H]2C[C@H](c3ccccc3)CN(C)C2)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C22H27N5O/c1-3-4-12-27-21(28)20-19(10-11-23-20)25-22(27)24-18-13-17(14-26(2)15-18)16-8-6-5-7-9-16/h3,5-11,17-18,23H,1,4,12-15H2,2H3,(H,24,25)/t17-,18+/m0/s1

Standard InChI Key:  VFFKPNVOCZLOJI-ZWKOTPCHSA-N

Molfile:  

 
     RDKit          2D

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   18.1144  -24.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1144  -25.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8238  -26.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5332  -25.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5332  -24.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8238  -24.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4041  -26.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6914  -25.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9806  -26.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9814  -26.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6988  -27.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4066  -26.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2445  -26.0645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8238  -23.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9569  -25.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6624  -26.0674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3743  -25.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9548  -24.8340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0853  -26.0705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6597  -24.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3741  -24.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9854  -24.2828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6504  -23.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8321  -23.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6602  -26.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9514  -27.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9493  -28.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2364  -28.5276    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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  2  7  1  6
  4 13  1  6
  6 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 21  1  0
 20 18  1  0
 18 15  2  0
 17 19  2  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
 16 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537244

   ---

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: 377.49

Molecular Weight (Monoisotopic): 377.2216

AlogP: 3.20

#Rotatable Bonds: 6

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: 12.00

CX Basic pKa: 7.92

CX LogP: 3.00

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.19

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