2-amino-3-(3-ethylphenyl)-4,5-dioxo-3,5-dihydro-4H-benzo[5,6]chromeno[3,4-c]pyridine-1-carbonitrile

ID: ALA5280355

Max Phase: Preclinical

Molecular Formula: C25H17N3O3

Molecular Weight: 407.43

Names and Identifiers

Canonical SMILES:  CCc1cccc(-n2c(N)c(C#N)c3c(c(=O)oc4ccc5ccccc5c43)c2=O)c1

Standard InChI:  InChI=1S/C25H17N3O3/c1-2-14-6-5-8-16(12-14)28-23(27)18(13-26)21-20-17-9-4-3-7-15(17)10-11-19(20)31-25(30)22(21)24(28)29/h3-12H,2,27H2,1H3

Standard InChI Key:  SMBACTKRCMCWOA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   -2.5013   -1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -2.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013   -2.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -2.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602   -0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -0.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -2.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3544    1.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -1.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7894    0.6198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7839    1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968    1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132    0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5014   -0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    2.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  2 10  1  0
  3 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  1  0
  4 14  1  0
 11 15  1  0
 16 15  2  0
 17 16  1  0
 18 17  1  0
 12 18  1  0
 13 19  2  0
 16 20  1  0
 18 21  2  0
 15 22  1  0
 22 23  3  0
 17 24  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 24 29  1  0
 26 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280355

   ---

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: 407.43

Molecular Weight (Monoisotopic): 407.1270

AlogP: 4.27

#Rotatable Bonds: 2

Polar Surface Area: 102.02

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -0.75

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