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

ID: ALA5289550

Max Phase: Preclinical

Molecular Formula: C15H12N4O4

Molecular Weight: 312.29

Names and Identifiers

Canonical SMILES:  COc1ccc(C2C(C#N)=C(N)Oc3[nH]c(=O)[nH]c(=O)c32)cc1

Standard InChI:  InChI=1S/C15H12N4O4/c1-22-8-4-2-7(3-5-8)10-9(6-16)12(17)23-14-11(10)13(20)18-15(21)19-14/h2-5,10H,17H2,1H3,(H2,18,19,20,21)

Standard InChI Key:  RJFJKSJXBIQQFI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -1.0719   -0.2049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750    0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750    1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584    2.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -0.6176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -2.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866   -2.6804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -2.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -2.6804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -2.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -2.6803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -1.4423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  3  4  1  0
  5  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  8 11  1  0
 11 12  1  0
 13  4  1  0
 14 13  1  0
 14 15  3  0
 16 13  2  0
 16 17  1  0
 18 16  1  0
 19 18  1  0
 19  3  2  0
 20 19  1  0
 21 20  1  0
 21 22  2  0
 23 21  1  0
 23  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289550

   ---

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: 312.29

Molecular Weight (Monoisotopic): 312.0859

AlogP: 0.29

#Rotatable Bonds: 2

Polar Surface Area: 133.99

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.31

CX LogP: 0.34

CX LogD: 0.29

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: -1.03

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