2-(benzo[d][1,3]dioxol-5-yl)-3-hydroxy-6-methoxy-4H-chromen-4-one

ID: ALA4552165

PubChem CID: 18372877

Max Phase: Preclinical

Molecular Formula: C17H12O6

Molecular Weight: 312.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2oc(-c3ccc4c(c3)OCO4)c(O)c(=O)c2c1

Standard InChI:  InChI=1S/C17H12O6/c1-20-10-3-5-12-11(7-10)15(18)16(19)17(23-12)9-2-4-13-14(6-9)22-8-21-13/h2-7,19H,8H2,1H3

Standard InChI Key:  FCBCQHFRLUWMPR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   25.2407   -3.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2396   -4.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9476   -4.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9458   -2.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6544   -3.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6552   -4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3637   -4.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0720   -4.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0673   -3.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3582   -2.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7777   -4.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7796   -5.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4880   -5.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4803   -4.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1893   -4.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1992   -5.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9830   -5.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4576   -4.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9670   -4.1774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3538   -2.0047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7725   -2.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5329   -2.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5327   -2.0101    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
  9 21  1  0
  1 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552165

   2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-6-methoxy-chromen-4-one

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: 312.28

Molecular Weight (Monoisotopic): 312.0634

AlogP: 2.90

#Rotatable Bonds: 2

Polar Surface Area: 78.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.80

CX Basic pKa: ┄

CX LogP: 2.19

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: 0.65

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