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

ID: ALA5290998

Max Phase: Preclinical

Molecular Formula: C14H9N5O5

Molecular Weight: 327.26

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)Oc2[nH]c(=O)[nH]c(=O)c2C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H9N5O5/c15-5-8-9(6-2-1-3-7(4-6)19(22)23)10-12(20)17-14(21)18-13(10)24-11(8)16/h1-4,9H,16H2,(H2,17,18,20,21)

Standard InChI Key:  AWTYFQJESBHIPF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    1.0708    0.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0708    1.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    1.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -1.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026   -0.4133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7876   -2.4773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576   -2.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -2.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -2.4774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877   -2.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -2.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877   -1.2387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -1.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857    1.6519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857    2.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.2391    0.0000 O   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
 22  2  1  0
 22 23  2  0
 22 24  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5290998

   ---

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: 327.26

Molecular Weight (Monoisotopic): 327.0604

AlogP: 0.19

#Rotatable Bonds: 2

Polar Surface Area: 167.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.31

CX LogP: 0.43

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -1.52

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