Diethyl (4,9-dioxo-2-(3,4,5-trimethoxyphenyl)-4,9-dihydrofuro[2,3-g]quinolin-3-yl)phosphonate

ID: ALA4878354

PubChem CID: 164626653

Max Phase: Preclinical

Molecular Formula: C24H24NO9P

Molecular Weight: 501.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)c1c(-c2cc(OC)c(OC)c(OC)c2)oc2c1C(=O)c1ncccc1C2=O

Standard InChI:  InChI=1S/C24H24NO9P/c1-6-32-35(28,33-7-2)24-17-20(27)18-14(9-8-10-25-18)19(26)23(17)34-21(24)13-11-15(29-3)22(31-5)16(12-13)30-4/h8-12H,6-7H2,1-5H3

Standard InChI Key:  MDRYGHYASPHLJR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   23.3215   -8.1496    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.1023   -8.4044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9292   -7.5987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4115   -9.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4103  -10.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1244  -10.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1226   -8.7905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8372   -9.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8407  -10.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5591  -10.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5523   -8.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5477   -7.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5613  -11.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2753   -9.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2770  -10.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0712  -10.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5603   -9.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0683   -8.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7687   -7.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552   -6.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3659   -6.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7154   -7.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4105   -8.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3844   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7928  -10.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6162  -10.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0276   -9.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6096   -8.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7875   -8.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0208   -8.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8516   -9.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0288  -11.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8449   -8.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2648  -10.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6164  -11.7467    0.0000 C   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
 10 15  1  0
 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
 28 30  1  0
 27 31  1  0
 26 32  1  0
 30 33  1  0
 31 34  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878354

   ---

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: 501.43

Molecular Weight (Monoisotopic): 501.1189

AlogP: 4.03

#Rotatable Bonds: 9

Polar Surface Area: 123.39

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.11

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: 0.35

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