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

ID: ALA4873161

PubChem CID: 164624821

Max Phase: Preclinical

Molecular Formula: C21H17FNO6P

Molecular Weight: 429.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)c1c(-c2ccc(F)cc2)oc2c1C(=O)c1ncccc1C2=O

Standard InChI:  InChI=1S/C21H17FNO6P/c1-3-27-30(26,28-4-2)21-15-18(25)16-14(6-5-11-23-16)17(24)20(15)29-19(21)12-7-9-13(22)10-8-12/h5-11H,3-4H2,1-2H3

Standard InChI Key:  JFTXQAZOJSLOGD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.5318  -18.7592    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.3126  -19.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1395  -18.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219  -19.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208  -20.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348  -21.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3330  -19.4001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0476  -19.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510  -20.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695  -21.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626  -19.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7581  -18.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717  -21.8761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4857  -19.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874  -20.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815  -20.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7706  -20.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788  -19.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790  -18.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656  -17.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5762  -16.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9258  -18.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7092  -18.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948  -20.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0031  -20.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8265  -20.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2379  -20.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8199  -19.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9980  -19.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0619  -20.2109    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873161

   ---

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: 429.34

Molecular Weight (Monoisotopic): 429.0778

AlogP: 4.15

#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: 2.64

CX LogD: 2.64

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -0.06

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