7-(2-chlorophenyl)-10,11-dihydro-6H-chromeno[4,3-b]quinoline-6,8(9H)-dione

ID: ALA5284245

Max Phase: Preclinical

Molecular Formula: C22H14ClNO3

Molecular Weight: 375.81

Names and Identifiers

Canonical SMILES:  O=C1CCCc2nc3c(c(-c4ccccc4Cl)c21)c(=O)oc1ccccc13

Standard InChI:  InChI=1S/C22H14ClNO3/c23-14-8-3-1-6-12(14)18-19-15(9-5-10-16(19)25)24-21-13-7-2-4-11-17(13)27-22(26)20(18)21/h1-4,6-8,11H,5,9-10H2

Standard InChI Key:  YLOJGDTYUWNABY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.4282    0.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145    0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145    1.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925    2.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282    1.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169    0.4041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -2.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1407   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532    0.3019    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -1.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -2.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7074   -2.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -1.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -0.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -0.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8526   -0.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8526   -1.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359   -2.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  0
  7  6  1  0
  2  7  1  0
  4  8  2  0
  9  8  1  0
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 10 11  1  0
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 21 19  1  0
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 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284245

   ---

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: 375.81

Molecular Weight (Monoisotopic): 375.0662

AlogP: 5.18

#Rotatable Bonds: 1

Polar Surface Area: 60.17

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.08

CX LogP: 4.53

CX LogD: 4.53

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.34

Np Likeness Score: -0.41

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