6-(4-bromophenyl)-3-(2-(2-hydroxyethoxy)ethyl)-7-phenyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

ID: ALA4282891

PubChem CID: 145981816

Max Phase: Preclinical

Molecular Formula: C22H20BrN3O3

Molecular Weight: 454.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2cc(-c3ccc(Br)cc3)n(-c3ccccc3)c2ncn1CCOCCO

Standard InChI:  InChI=1S/C22H20BrN3O3/c23-17-8-6-16(7-9-17)20-14-19-21(26(20)18-4-2-1-3-5-18)24-15-25(22(19)28)10-12-29-13-11-27/h1-9,14-15,27H,10-13H2

Standard InChI Key:  ZVUYOGCMZKVMGS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.0510  -12.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0482  -11.5443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3396  -11.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6333  -12.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6300  -11.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8524  -11.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3751  -11.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8578  -12.6229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5625  -11.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1516  -11.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3352  -11.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9286  -11.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3445  -12.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1596  -12.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6081  -13.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8081  -13.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5586  -14.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1081  -14.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9103  -14.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1561  -14.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3369  -10.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7543  -11.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4636  -11.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1698  -11.1278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8790  -11.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5852  -11.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2944  -11.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1115  -11.9780    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
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 13 14  1  0
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 15 10  1  0
  8 10  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  9 16  1  0
  4 22  2  0
  3 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 13 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4282891

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.32

Molecular Weight (Monoisotopic): 453.0688

AlogP: 3.63

#Rotatable Bonds: 7

Polar Surface Area: 69.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.16

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.14

References

1. Pathania S, Rawal RK..  (2018)  Pyrrolopyrimidines: An update on recent advancements in their medicinal attributes.,  157  [PMID:30114661] [10.1016/j.ejmech.2018.08.023]

Source

Source(1):

• Scientific Literature