4-(benzylamino)-2-(methylthio)-7-oxo-6-phenyl-7H-pyrrolo[3,2-d]pyrimidine 5-oxide

ID: ALA604269

PubChem CID: 25149168

Max Phase: Preclinical

Molecular Formula: C20H16N4O2S

Molecular Weight: 376.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(NCc2ccccc2)c2c(n1)C(=O)C(c1ccccc1)=[N+]2[O-]

Standard InChI:  InChI=1S/C20H16N4O2S/c1-27-20-22-15-17(19(23-20)21-12-13-8-4-2-5-9-13)24(26)16(18(15)25)14-10-6-3-7-11-14/h2-11H,12H2,1H3,(H,21,22,23)

Standard InChI Key:  OXUMHAYBHOACHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -4.1056   -9.2458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068  -10.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919  -10.4860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3937   -8.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784   -9.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6735  -10.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816  -10.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3970   -9.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -8.9807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750  -11.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -9.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580  -10.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662  -10.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0753   -9.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -8.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -8.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962   -8.0080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5288   -8.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8196  -10.4859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203  -11.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119   -7.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144   -6.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -6.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034   -5.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1197   -5.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8353   -5.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8296   -6.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
  6  7  1  0
  4 17  1  0
  7  8  1  0
  9 18  1  0
  8  9  2  0
  9  5  1  0
 19 20  1  0
  2 19  1  0
  4  1  1  0
 17 21  1  0
  7 10  2  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 24  1  0
 11 12  2  0
 24 25  2  0
  2  3  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 22  1  0
M  CHG  2   9   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA604269

   4-(Benzylamino)-2-methylsulfanyl-5-oxido-6-phenylpyrrolo[3,2-d]pyrimidin-5-ium-7-one

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: 376.44

Molecular Weight (Monoisotopic): 376.0994

AlogP: 3.64

#Rotatable Bonds: 5

Polar Surface Area: 80.95

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.19

CX Basic pKa: 0.28

CX LogP: 2.08

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.75

References

1. Pudziuvelyte E, Ríos-Luci C, León LG, Cikotiene I, Padrón JM..  (2009)  Synthesis and antiproliferative activity of 2,4-disubstituted 6-aryl-7H-pyrrolo[3,2-d]pyrimidin-7-one 5-oxides.,  17  (14): [PMID:19527934] [10.1016/j.bmc.2009.05.078]

Source

Source(1):

• Scientific Literature