Diethyl (2-(2-chlorophenyl)-4,9-dioxo-4,9-dihydrofuro[3,2-g]quinolin-3-yl)phosphonate

ID: ALA4874926

PubChem CID: 164625926

Max Phase: Preclinical

Molecular Formula: C21H17ClNO6P

Molecular Weight: 445.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)c1c(-c2ccccc2Cl)oc2c1C(=O)c1cccnc1C2=O

Standard InChI:  InChI=1S/C21H17ClNO6P/c1-3-27-30(26,28-4-2)21-15-17(24)13-9-7-11-23-16(13)18(25)20(15)29-19(21)12-8-5-6-10-14(12)22/h5-11H,3-4H2,1-2H3

Standard InChI Key:  UYRVGTJYLSZODF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   33.0551  -18.0214    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   33.8357  -18.2763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6628  -17.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1454  -19.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1442  -19.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8582  -20.3135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8564  -18.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5710  -19.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5744  -19.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2928  -20.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2860  -18.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2814  -17.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2951  -21.1380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0089  -19.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0106  -19.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8048  -20.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2939  -19.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8020  -18.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5024  -17.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4888  -16.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0994  -16.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4489  -17.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2324  -17.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1180  -19.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5263  -20.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3496  -20.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7610  -19.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3430  -18.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5210  -18.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1112  -20.9028    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
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 15 16  1  0
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 17 18  2  0
 18 14  1  0
 18  1  1  0
  1 19  2  0
  3 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874926

   ---

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: 445.80

Molecular Weight (Monoisotopic): 445.0482

AlogP: 4.66

#Rotatable Bonds: 6

Polar Surface Area: 95.70

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.87

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -0.12

References

1. Modranka J, Drogosz-Stachowicz J, Pietrzak A, Janecka A, Janecki T..  (2021)  Synthesis and structure-activity relationship study of novel 3-diethoxyphosphorylfuroquinoline-4,9-diones with potent antitumor efficacy.,  219  [PMID:33852973] [10.1016/j.ejmech.2021.113429]

Source

Source(1):

• Scientific Literature