2-(benzo[d][1,3]dioxol-5-yl)-7-methoxy-3-propoxy-4H-chromen-4-one

ID: ALA4476298

PubChem CID: 155538251

Max Phase: Preclinical

Molecular Formula: C20H18O6

Molecular Weight: 354.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCOc1c(-c2ccc3c(c2)OCO3)oc2cc(OC)ccc2c1=O

Standard InChI:  InChI=1S/C20H18O6/c1-3-8-23-20-18(21)14-6-5-13(22-2)10-16(14)26-19(20)12-4-7-15-17(9-12)25-11-24-15/h4-7,9-10H,3,8,11H2,1-2H3

Standard InChI Key:  MMGZIPGOSYBDQG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   15.4674   -3.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4663   -4.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1743   -4.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1725   -3.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8812   -3.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8819   -4.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5905   -4.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2987   -4.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2940   -3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5849   -3.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0045   -4.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0063   -5.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7148   -6.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7070   -4.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4160   -4.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4259   -5.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2097   -5.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6844   -5.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1938   -4.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5805   -2.3803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7583   -4.8389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0509   -4.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9992   -3.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7094   -3.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4146   -3.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1248   -3.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 16  2  0
 15 14  2  0
 14 11  1  0
  8 11  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 10 20  2  0
  2 21  1  0
 21 22  1  0
  9 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476298

   ---

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: 354.36

Molecular Weight (Monoisotopic): 354.1103

AlogP: 3.99

#Rotatable Bonds: 5

Polar Surface Area: 67.13

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.18

CX LogD: 3.18

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: 0.26

References

1. Borsari C, Santarem N, Macedo S, Jiménez-Antón MD, Torrado JJ, Olías-Molero AI, Corral MJ, Tait A, Ferrari S, Costantino L, Luciani R, Ponterini G, Gul S, Kuzikov M, Ellinger B, Behrens B, Reinshagen J, Alunda JM, Cordeiro-da-Silva A, Costi MP..  (2019)  SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-Trypanosoma brucei Agent.,  10  (4): [PMID:30996791] [10.1021/acsmedchemlett.8b00565]

Source

Source(1):

• Scientific Literature