3-hydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one

ID: ALA242172

Cas Number: 55977-09-8

PubChem CID: 676295

Max Phase: Preclinical

Molecular Formula: C15H10O4

Molecular Weight: 254.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,3'-Dihydroxy Flavone | 3-Hydroxyflavonol | 3,3'-DIHYDROXYFLAVONE|55977-09-8|3-hydroxy-2-(3-hydroxyphenyl)chromen-4-one|TNP00067|3'-hydroxyflavonol|3-Hydroxyflavonol|3,3'-Dihydroxy Flavone|SCHEMBL345657|CHEMBL242172|DTXSID70350266|QZESEGHSLFKZIV-UHFFFAOYSA-N|MFCD01630877|NSC792746|AKOS024282380|NSC-792746|NCGC00017202-01|NCGC00017202-02|NCGC00142428-01|NS00116233|3-hydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one|Q63399153|4H-1-Benzopyran-4-one, 3-hydroxy-2-(3-hydroxyphenyl)-

Canonical SMILES:  O=c1c(O)c(-c2cccc(O)c2)oc2ccccc12

Standard InChI:  InChI=1S/C15H10O4/c16-10-5-3-4-9(8-10)15-14(18)13(17)11-6-1-2-7-12(11)19-15/h1-8,16,18H

Standard InChI Key:  QZESEGHSLFKZIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -4.3950   -7.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -8.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6817   -9.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6835   -7.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -7.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9677   -8.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2528   -9.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5381   -8.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -7.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2584   -7.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -9.9498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344   -7.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174   -7.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937   -7.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891   -6.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325   -6.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -6.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404   -5.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8225   -9.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  9 10  1  0
 10  5  1  0
  7 11  2  0
  2  3  1  0
  5  6  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  5  4  2  0
 16 18  1  0
  8  9  2  0
  8 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA242172

   3,3'-Dihydroxyflavone

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: 254.24

Molecular Weight (Monoisotopic): 254.0579

AlogP: 2.87

#Rotatable Bonds: 1

Polar Surface Area: 70.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.74

CX Basic pKa: ┄

CX LogP: 2.42

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.70

Np Likeness Score: 0.86

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. Qin CX, Chen X, Hughes RA, Williams SJ, Woodman OL..  (2008)  Understanding the cardioprotective effects of flavonols: discovery of relaxant flavonols without antioxidant activity.,  51  (6): [PMID:18307286] [10.1021/jm070352h]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Liu X, Chan CB, Jang SW, Pradoldej S, Huang J, He K, Phun LH, France S, Xiao G, Jia Y, Luo HR, Ye K..  (2010)  A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect.,  53  (23): [PMID:21073191] [10.1021/jm101206p]

6. PubChem BioAssay data set, 

7. 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