7-amino-5-(4-bromophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile

ID: ALA5278869

Max Phase: Preclinical

Molecular Formula: C14H9BrN4O3

Molecular Weight: 361.15

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)Oc2[nH]c(=O)[nH]c(=O)c2C1c1ccc(Br)cc1

Standard InChI:  InChI=1S/C14H9BrN4O3/c15-7-3-1-6(2-4-7)9-8(5-16)11(17)22-13-10(9)12(20)18-14(21)19-13/h1-4,9H,17H2,(H2,18,19,20,21)

Standard InChI Key:  GBROIDUZYDLBLJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.0756    0.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756    1.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026   -0.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876   -2.4756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -2.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -2.4756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877   -2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -2.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877   -1.2370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726    0.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    2.4756    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  8  7  1  0
  9  8  1  0
  9 10  3  0
 11  8  2  0
 11 12  1  0
 13 11  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 16 17  2  0
 18 16  1  0
 18 19  1  0
 19 20  2  0
 21 19  1  0
 21  7  1  0
 14 21  2  0
  3 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278869

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 361.15

Molecular Weight (Monoisotopic): 359.9858

AlogP: 1.04

#Rotatable Bonds: 1

Polar Surface Area: 124.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: 1.31

CX LogP: 1.26

CX LogD: 1.23

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: -1.19

References

1. Elattar KM, El-Khateeb AY, Hamed SE..  (2022)  Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs.,  13  (5.0): [PMID:35694689] [10.1039/d2md00076h]

Source

Source(1):

• Scientific Literature