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

ID: ALA395808

Chembl Id: CHEMBL395808

PubChem CID: 676035

Max Phase: Preclinical

Molecular Formula: C16H12O4

Molecular Weight: 268.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2cc(=O)c3ccccc3o2)ccc1O

Standard InChI:  InChI=1S/C16H12O4/c1-19-16-8-10(6-7-12(16)17)15-9-13(18)11-4-2-3-5-14(11)20-15/h2-9,17H,1H3

Standard InChI Key:  KTFLFGFPJQSPNR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA395808

   4'-Hydroxy-3'-Methoxyflavone

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: 268.27

Molecular Weight (Monoisotopic): 268.0736

AlogP: 3.17

#Rotatable Bonds: 2

Polar Surface Area: 59.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 2.51

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.78

Np Likeness Score: 0.69

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. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Shin SY, Woo Y, Hyun J, Yong Y, Koh D, Lee YH, Lim Y..  (2011)  Relationship between the structures of flavonoids and their NF-κB-dependent transcriptional activities.,  21  (20): [PMID:21907578] [10.1016/j.bmcl.2011.08.077]

6. PubChem BioAssay data set, 

7. Golub AG, Bdzhola VG, Ostrynska OV, Kyshenia IV, Sapelkin VM, Prykhod'ko AO, Kukharenko OP, Yarmoluk SM..  (2013)  Discovery and characterization of synthetic 4'-hydroxyflavones-New CK2 inhibitors from flavone family.,  21  (21): [PMID:24011954] [10.1016/j.bmc.2013.08.013]

8. Amrutha K, Nanjan P, Shaji SK, Sunilkumar D, Subhalakshmi K, Rajakrishna L, Banerji A..  (2014)  Discovery of lesser known flavones as inhibitors of NF-κB signaling in MDA-MB-231 breast cancer cells--A SAR study.,  24  (19): [PMID:25190466] [10.1016/j.bmcl.2014.07.093]

9. 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]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays