3,6-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

ID: ALA243676

Cas Number: 253195-19-6

PubChem CID: 676308

Max Phase: Preclinical

Molecular Formula: C15H10O5

Molecular Weight: 270.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c(O)c(-c2ccc(O)cc2)oc2ccc(O)cc12

Standard InChI:  InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-14(19)13(18)11-7-10(17)5-6-12(11)20-15/h1-7,16-17,19H

Standard InChI Key:  QUPHEKFURGDWME-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   11.3710   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3699   -4.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0843   -5.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0825   -3.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7975   -4.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7963   -4.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5128   -5.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2349   -4.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2361   -4.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5152   -3.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5104   -6.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9495   -3.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6628   -4.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3774   -3.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3799   -2.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6618   -2.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9502   -2.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9478   -5.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6555   -5.2612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0944   -2.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
  5  6  1  0
  7 11  2  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  5 10  1  0
  8 18  1  0
  6  7  1  0
  2 19  1  0
  7  8  1  0
 15 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA243676

   3,6,4'-Trihydroxyflavone

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 270.24

Molecular Weight (Monoisotopic): 270.0528

AlogP: 2.58

#Rotatable Bonds: 1

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.31

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 2.06

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: 0.99

References

1. Khlebnikov AI, Schepetkin IA, Domina NG, Kirpotina LN, Quinn MT..  (2007)  Improved quantitative structure-activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems.,  15  (4): [PMID:17166721] [10.1016/j.bmc.2006.11.037]

2. Lee JY, Jeong KW, Shin S, Lee JU, Kim Y..  (2009)  Antimicrobial natural products as beta-ketoacyl-acyl carrier protein synthase III inhibitors.,  17  (15): [PMID:19595597] [10.1016/j.bmc.2009.06.059]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Borsari C, Luciani R, Pozzi C, Poehner I, Henrich S, Trande M, Cordeiro-da-Silva A, Santarem N, Baptista C, Tait A, Di Pisa F, Dello Iacono L, Landi G, Gul S, Wolf M, Kuzikov M, Ellinger B, Reinshagen J, Witt G, Gribbon P, Kohler M, Keminer O, Behrens B, Costantino L, Tejera Nevado P, Bifeld E, Eick J, Clos J, Torrado J, Jiménez-Antón MD, Corral MJ, Alunda JM, Pellati F, Wade RC, Ferrari S, Mangani S, Costi MP..  (2016)  Profiling of Flavonol Derivatives for the Development of Antitrypanosomatidic Drugs.,  59  (16): [PMID:27411733] [10.1021/acs.jmedchem.6b00698]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays