8-amino-7-(4-bromophenyl)-8,9-dihydro-6H,7H-chromeno[3',4':5,6]pyrano[2,3-d]pyrimidin-6-one

ID: ALA5281677

Max Phase: Preclinical

Molecular Formula: C20H14BrN3O3

Molecular Weight: 424.25

Names and Identifiers

Canonical SMILES:  NC1NC=NC2=C1C(c1ccc(Br)cc1)c1c(c3ccccc3oc1=O)O2

Standard InChI:  InChI=1S/C20H14BrN3O3/c21-11-7-5-10(6-8-11)14-15-17(27-19-16(14)18(22)23-9-24-19)12-3-1-2-4-13(12)26-20(15)25/h1-9,14,18H,22H2,(H,23,24)

Standard InChI Key:  YJVGAFBGULKMPT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   -1.0745    0.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -0.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529   -0.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    1.6540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    2.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    1.6705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.4247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -1.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4960   -1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4960   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7839   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -2.0628    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529   -1.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -2.0706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818   -1.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818   -0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -0.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -1.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4939   -2.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3638   -2.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  6  5  2  0
  6  1  1  0
  6  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  1  0
  5 10  1  0
 10 11  1  0
 12  4  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 15 18  1  0
 19  3  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 21 26  1  0
 27 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281677

   ---

Molecule Features

Natural Product: Yes

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: 424.25

Molecular Weight (Monoisotopic): 423.0219

AlogP: 3.21

#Rotatable Bonds: 1

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.56

CX LogP: 2.48

CX LogD: 2.09

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: 0.13

References

1. Salehian F, Nadri H, Jalili-Baleh L, Youseftabar-Miri L, Abbas Bukhari SN, Foroumadi A, Tüylü Küçükkilinç T, Sharifzadeh M, Khoobi M..  (2021)  A review: Biologically active 3,4-heterocycle-fused coumarins.,  212  [PMID:33276991] [10.1016/j.ejmech.2020.113034]

Source

Source(1):

• Scientific Literature