3-Methyl-2-{[(1R,3r,5S)-9-[(2R)-2-hydroxy-2-phenylethyl]-9-azabicyclo[3.3.1]nonan-3-yl]amino}-3H,4H,5H-pyrrolo[3,2-d]-pyrimidin-4-one

ID: ALA4547880

PubChem CID: 155554161

Max Phase: Preclinical

Molecular Formula: C23H29N5O2

Molecular Weight: 407.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(N[C@H]2C[C@H]3CCC[C@@H](C2)N3C[C@H](O)c2ccccc2)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C23H29N5O2/c1-27-22(30)21-19(10-11-24-21)26-23(27)25-16-12-17-8-5-9-18(13-16)28(17)14-20(29)15-6-3-2-4-7-15/h2-4,6-7,10-11,16-18,20,24,29H,5,8-9,12-14H2,1H3,(H,25,26)/t16-,17+,18-,20-/m0/s1

Standard InChI Key:  QNDMHXNFQXCORG-DMUMMCEESA-N

Molfile:  

 
     RDKit          2D

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    9.8950  -19.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3279  -19.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6088  -18.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9381  -18.2748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0446  -20.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0318  -18.8083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7472  -20.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9828  -18.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2599  -18.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5570  -18.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357  -19.5889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828  -17.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850  -17.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1568  -17.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1351  -18.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379  -18.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7366  -17.5878    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139  -20.3523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
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  9 15  2  0
  7 16  1  0
  8 17  1  0
 18 16  1  6
 18 19  1  0
 18 21  1  0
 19  4  1  0
  4 20  1  0
  3 20  1  0
  3 21  1  0
 20 22  1  0
 22 23  1  0
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 23 25  1  6
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 24  1  0
  4 31  1  1
  3 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4547880

   ---

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: 407.52

Molecular Weight (Monoisotopic): 407.2321

AlogP: 2.79

#Rotatable Bonds: 5

Polar Surface Area: 86.18

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.00

CX Basic pKa: 9.01

CX LogP: 2.09

CX LogD: 0.45

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.61

Np Likeness Score: -0.39

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