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

ID: ALA4539318

PubChem CID: 155549995

Max Phase: Preclinical

Molecular Formula: C21H25N5O

Molecular Weight: 363.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCN1C[C@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@H](c2ccccc2)C1

Standard InChI:  InChI=1S/C21H25N5O/c1-3-11-26-13-16(15-7-5-4-6-8-15)12-17(14-26)23-21-24-18-9-10-22-19(18)20(27)25(21)2/h3-10,16-17,22H,1,11-14H2,2H3,(H,23,24)/t16-,17+/m0/s1

Standard InChI Key:  NKLONURTQFZVHM-DLBZAZTESA-N

Molfile:  

 
     RDKit          2D

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   27.1530   -4.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1530   -5.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8583   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5636   -5.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5636   -4.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8583   -3.9952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2707   -5.6347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9790   -5.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6845   -5.6376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3923   -5.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9769   -4.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6818   -4.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3898   -4.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0001   -3.8686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6692   -3.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8545   -3.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1002   -5.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6823   -6.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4459   -5.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7383   -5.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0317   -5.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0324   -6.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7457   -6.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4494   -6.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8583   -3.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5660   -2.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5660   -1.9522    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
 10 13  1  0
 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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539318

   ---

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: 363.47

Molecular Weight (Monoisotopic): 363.2059

AlogP: 2.72

#Rotatable Bonds: 5

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: 12.01

CX Basic pKa: 7.55

CX LogP: 2.71

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -0.57

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