3,6,3',4'-Tetrahydroxyflavone

ID: ALA1224325

PubChem CID: 667581

Max Phase: Preclinical

Molecular Formula: C15H10O6

Molecular Weight: 286.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,6,3',4'-Tetrahydroxyflavone | 3,6,3',4'-TETRAHYDROXYFLAVONE|2-(3,4-Dihydroxyphenyl)-3,6-Dihydroxy-4h-1-Benzopyran-4-One|SCHEMBL505584|CHEMBL1224325|AKOS024283045|Q27456424|2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-4H-chromen-4-one|4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-|6JM

Canonical SMILES:  O=c1c(O)c(-c2ccc(O)c(O)c2)oc2ccc(O)cc12

Standard InChI:  InChI=1S/C15H10O6/c16-8-2-4-12-9(6-8)13(19)14(20)15(21-12)7-1-3-10(17)11(18)5-7/h1-6,16-18,20H

Standard InChI Key:  BXPBSBBFPNTFFT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
 10 11  1  0
  1 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 15 18  1  0
 14 19  1  0
  7 20  1  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1224325

   3,6,3',4'-Tetrahydroxyflavone

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: 286.24

Molecular Weight (Monoisotopic): 286.0477

AlogP: 2.28

#Rotatable Bonds: 1

Polar Surface Area: 111.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: 1.81

CX LogD: 1.75

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 1.29

References

1. Hyun J, Woo Y, Hwang DS, Jo G, Eom S, Lee Y, Park JC, Lim Y..  (2010)  Relationships between structures of hydroxyflavones and their antioxidative effects.,  20  (18): [PMID:20692831] [10.1016/j.bmcl.2010.07.068]

2. 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(1):

• Scientific Literature