2-{[(3R,5R)-5-[4-chloro-3-(trifluoromethyl)phenyl]-1-methylpiperidin-3-yl]amino}-3-methyl-3H,4H,5H-pyrrolo[3,2-d]-pyrimidin-4-one

ID: ALA4527339

PubChem CID: 155544332

Max Phase: Preclinical

Molecular Formula: C20H21ClF3N5O

Molecular Weight: 439.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@H](Nc2nc3cc[nH]c3c(=O)n2C)C[C@H](c2ccc(Cl)c(C(F)(F)F)c2)C1

Standard InChI:  InChI=1S/C20H21ClF3N5O/c1-28-9-12(11-3-4-15(21)14(8-11)20(22,23)24)7-13(10-28)26-19-27-16-5-6-25-17(16)18(30)29(19)2/h3-6,8,12-13,25H,7,9-10H2,1-2H3,(H,26,27)/t12-,13+/m0/s1

Standard InChI Key:  POPPPIOICRXWNP-QWHCGFSZSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   19.6415  -20.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6415  -21.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3468  -22.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0520  -21.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0520  -20.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3468  -20.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7592  -22.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4675  -21.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1729  -22.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8807  -21.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4654  -20.8058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1703  -20.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8783  -20.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4885  -20.2619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1576  -19.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3430  -19.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5887  -22.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1708  -22.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9344  -22.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2267  -21.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5201  -22.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5208  -22.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2341  -23.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9378  -22.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3468  -19.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8143  -23.2568    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.8120  -21.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8112  -20.8031    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1047  -22.0296    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1003  -21.2098    0.0000 F   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
 22 26  1  0
 21 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527339

   ---

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: 439.87

Molecular Weight (Monoisotopic): 439.1387

AlogP: 3.83

#Rotatable Bonds: 3

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: 7.51

CX LogP: 3.46

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -0.70

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