4-hydroxy-3-methoxyflavonol

ID: ALA271321

Chembl Id: CHEMBL271321

PubChem CID: 625119

Max Phase: Preclinical

Molecular Formula: C16H12O5

Molecular Weight: 284.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2oc3ccccc3c(=O)c2O)ccc1O

Standard InChI:  InChI=1S/C16H12O5/c1-20-13-8-9(6-7-11(13)17)16-15(19)14(18)10-4-2-3-5-12(10)21-16/h2-8,17,19H,1H3

Standard InChI Key:  YONDROKMQHIDPQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA271321

   3-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

Molecule Features

Natural Product: No

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: 284.27

Molecular Weight (Monoisotopic): 284.0685

AlogP: 2.88

#Rotatable Bonds: 2

Polar Surface Area: 79.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.73

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.76

Np Likeness Score: 0.91

References

1. 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]

2. Ma ML, Li M, Gou JJ, Ruan TY, Jin HS, Zhang LH, Wu LC, Li XY, Hu YH, Wen K, Zhao Z..  (2014)  Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor.,  22  (21): [PMID:25262941] [10.1016/j.bmc.2014.08.038]

3. Venkateswararao E, Son MJ, Sharma N, Manickam M, Boggu P, Kim YH, Woo SH, Jung SH..  (2015)  Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction.,  6  (7): [PMID:26191362] [10.1021/acsmedchemlett.5b00043]

4. Estévez-Sarmiento F, Said M, Brouard I, León F, García C, Quintana J, Estévez F..  (2017)  3'-Hydroxy-3,4'-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells.,  25  (21): [PMID:29032930] [10.1016/j.bmc.2017.09.043]

Source

Source(1):

• Scientific Literature