ID: ALA244707

Max Phase: Preclinical

Molecular Formula: C15H10O5

Molecular Weight: 270.24

Molecule Type: Small molecule

Representations

Synonyms (3): 7,8,2'-Trihydroxy Flavone | 7,8,2'-Trihydroxyflavanone | 7,8,2'-Trihydroxyflavone
Synonyms from Alternative Forms(3):

Canonical SMILES:  O=c1cc(-c2ccccc2O)oc2c(O)c(O)ccc12

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

Standard InChI Key:  JHGZYXRWZXMYBZ-UHFFFAOYSA-N

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

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: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.72

CX Basic pKa:

CX LogP: 2.06

CX LogD: 1.26

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.59

Np Likeness Score: 1.08

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. Bisson WH, Koch DC, O'Donnell EF, Khalil SM, Kerkvliet NI, Tanguay RL, Abagyan R, Kolluri SK..  (2009)  Modeling of the aryl hydrocarbon receptor (AhR) ligand binding domain and its utility in virtual ligand screening to predict new AhR ligands.,  52  (18): [PMID:19719119] [10.1021/jm900199u]

3. 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]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. 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]

7. PubChem BioAssay data set, 

8. Liu MM, Zhou L, He PL, Zhang YN, Zhou JY, Shen Q, Chen XW, Zuo JP, Li W, Ye DY..  (2012)  Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.,  52  [PMID:22445328] [10.1016/j.ejmech.2012.03.002]

9. Kim YS, Keyser SG, Schneekloth JS..  (2014)  Synthesis of 2',3',4'-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation.,  24  (4): [PMID:24468414] [10.1016/j.bmcl.2014.01.010]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays