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

ID: ALA4874138

PubChem CID: 164627160

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)c1ncccc1C2=O

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

Standard InChI Key:  YGTDHBLIRUYMOS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.4992  -24.2519    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800  -24.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070  -23.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895  -25.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5884  -26.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024  -26.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007  -24.8928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153  -25.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187  -26.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370  -26.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302  -24.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7257  -24.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393  -27.3686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532  -25.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549  -26.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2490  -26.3863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381  -25.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462  -25.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9466  -23.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331  -22.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5436  -22.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932  -23.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6765  -24.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622  -25.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9705  -26.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7938  -26.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2053  -25.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7873  -24.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9653  -24.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554  -27.1335    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
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 10  1  0
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 14 11  1  0
 11 12  2  0
 10 13  2  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 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:

   

   ALA4874138

   ---

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: 1.11

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -0.03

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