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

ID: ALA4285244

PubChem CID: 145992612

Max Phase: Preclinical

Molecular Formula: C21H18BrN3O3

Molecular Weight: 440.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2cc(-c3ccc(Br)cc3)n(-c3ccccc3)c2ncn1CC(O)CO

Standard InChI:  InChI=1S/C21H18BrN3O3/c22-15-8-6-14(7-9-15)19-10-18-20(25(19)16-4-2-1-3-5-16)23-13-24(21(18)28)11-17(27)12-26/h1-10,13,17,26-27H,11-12H2

Standard InChI Key:  PUNNAAHSQXDGSS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   26.3480  -12.7806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0576  -12.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0548  -11.5485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3462  -11.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6399  -12.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6366  -11.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8590  -11.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3817  -11.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8644  -12.6270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5691  -11.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1582  -11.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3418  -11.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9352  -11.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3511  -12.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1662  -12.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6147  -13.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8147  -13.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5652  -14.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1147  -14.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9169  -14.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1627  -14.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3435  -10.3260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7610  -11.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4702  -11.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1764  -11.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4733  -12.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8856  -11.5378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1181  -11.9821    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
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 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
 24 26  1  0
 25 27  1  0
 13 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4285244

   ---

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: 440.30

Molecular Weight (Monoisotopic): 439.0532

AlogP: 2.97

#Rotatable Bonds: 5

Polar Surface Area: 80.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 1.21

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -0.91

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