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

ID: ALA4579627

PubChem CID: 155565166

Max Phase: Preclinical

Molecular Formula: C20H25N5O

Molecular Weight: 351.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCn1c(N[C@@H]2C[C@H](c3ccccc3)CN(C)C2)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C20H25N5O/c1-3-25-19(26)18-17(9-10-21-18)23-20(25)22-16-11-15(12-24(2)13-16)14-7-5-4-6-8-14/h4-10,15-16,21H,3,11-13H2,1-2H3,(H,22,23)/t15-,16+/m0/s1

Standard InChI Key:  LUPOEXSMBVBUPV-JKSUJKDBSA-N

Molfile:  

 
     RDKit          2D

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   30.8510  -18.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8510  -18.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5604  -19.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2698  -18.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2698  -18.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5604  -17.6191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1407  -19.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4280  -18.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7173  -19.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7180  -20.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4354  -20.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1433  -20.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9811  -19.2669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5604  -16.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6935  -18.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3990  -19.2699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1109  -18.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6914  -18.0364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8220  -19.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3963  -17.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1107  -18.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7221  -17.4811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3870  -16.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5687  -16.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3968  -20.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6881  -20.4979    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
M  END

Alternative Forms

1. Parent:

   

   ALA4579627

   ---

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: 351.45

Molecular Weight (Monoisotopic): 351.2059

AlogP: 2.64

#Rotatable Bonds: 4

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: 7.91

CX LogP: 2.34

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -0.49

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