2-amino-5-oxo-4-(quinolin-3-yl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

ID: ALA4870551

PubChem CID: 164621545

Max Phase: Preclinical

Molecular Formula: C22H13N3O3

Molecular Weight: 367.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)Oc2c(c(=O)oc3ccccc23)C1c1cnc2ccccc2c1

Standard InChI:  InChI=1S/C22H13N3O3/c23-10-15-18(13-9-12-5-1-3-7-16(12)25-11-13)19-20(28-21(15)24)14-6-2-4-8-17(14)27-22(19)26/h1-9,11,18H,24H2

Standard InChI Key:  GEIMEDSMTHKZAK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.6934   -4.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4072   -5.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4054   -3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1198   -4.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1186   -4.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8344   -5.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5561   -4.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8369   -3.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5572   -4.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2797   -3.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2881   -2.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5677   -2.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8389   -2.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2684   -5.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5745   -1.5173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0029   -2.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7199   -1.9549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9885   -4.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9800   -4.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6891   -5.2580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7019   -3.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4115   -4.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4062   -4.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1173   -5.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8342   -4.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8356   -4.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1238   -3.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
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  7  8  1  0
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  9 10  2  0
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 10 11  1  0
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 12 13  2  0
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  8 15  2  0
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 12 17  1  0
 19 20  2  0
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 23 22  2  0
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 11 19  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870551

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.36

Molecular Weight (Monoisotopic): 367.0957

AlogP: 3.56

#Rotatable Bonds: 1

Polar Surface Area: 102.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.20

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.78

References

1. Sarkate AP, Dofe VS, Tiwari SV, Lokwani DK, Karnik KS, Kamble DD, Ansari MHSH, Dodamani S, Jalalpure SS, Sangshetti JN, Azad R, Burra PVLS, Bhandari SV..  (2021)  One pot synthesis, in silico study and evaluation of some novel flavonoids as potent topoisomerase II inhibitors.,  40  [PMID:33689875] [10.1016/j.bmcl.2021.127916]

Source

Source(1):

• Scientific Literature