2-((3S,5S)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-methylpiperidin-3-ylamino)-3-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

ID: ALA4581184

PubChem CID: 155561271

Max Phase: Preclinical

Molecular Formula: C21H25N5O3

Molecular Weight: 395.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@@H](c2ccc3c(c2)OCCO3)C1

Standard InChI:  InChI=1S/C21H25N5O3/c1-25-11-14(13-3-4-17-18(10-13)29-8-7-28-17)9-15(12-25)23-21-24-16-5-6-22-19(16)20(27)26(21)2/h3-6,10,14-15,22H,7-9,11-12H2,1-2H3,(H,23,24)/t14-,15+/m1/s1

Standard InChI Key:  PUFPGLSWMMJNSE-CABCVRRESA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   32.3740  -10.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3740  -11.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0834  -12.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7928  -11.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7928  -10.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0834  -10.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5040  -12.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2123  -11.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9219  -12.1174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6339  -11.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2103  -10.8839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9193  -10.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6314  -10.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2458  -10.3401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9149   -9.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0961   -9.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3459  -12.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9198  -12.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6627  -12.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9510  -11.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9584  -13.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6662  -12.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0834   -9.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2410  -12.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2402  -12.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5323  -11.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8247  -12.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8254  -12.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5337  -13.3481    0.0000 O   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  1
  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  1
 19 20  2  0
 20 25  1  0
 24 21  1  0
 21 22  2  0
 22 19  1  0
  6 23  1  0
 24 25  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4581184

   ---

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: 395.46

Molecular Weight (Monoisotopic): 395.1957

AlogP: 1.93

#Rotatable Bonds: 3

Polar Surface Area: 84.41

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 7.47

CX LogP: 1.49

CX LogD: 1.14

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: -0.28

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