6-[5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxy-phenyl)-chromen-4-one

ID: ALA63677

Chembl Id: CHEMBL63677

Max Phase: Preclinical

Molecular Formula: C30H18O10

Molecular Weight: 538.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Robustaflavone

Canonical SMILES:  O=c1cc(-c2ccc(O)c(-c3c(O)cc4oc(-c5ccc(O)cc5)cc(=O)c4c3O)c2)oc2cc(O)cc(O)c12

Standard InChI:  InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)23-11-22(37)29-26(39-23)12-20(35)27(30(29)38)17-7-14(3-6-18(17)33)24-10-21(36)28-19(34)8-16(32)9-25(28)40-24/h1-12,31-35,38H

Standard InChI Key:  BORWSEZUWHQTOK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA63677

   ROBUSTAFLAVONE

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: 538.46

Molecular Weight (Monoisotopic): 538.0900

AlogP: 5.13

#Rotatable Bonds: 3

Polar Surface Area: 181.80

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.06

CX Basic pKa: ┄

CX LogP: 5.09

CX LogD: 2.77

Aromatic Rings: 6

Heavy Atoms: 40

QED Weighted: 0.18

Np Likeness Score: 1.18

References

1. Lin YM, Flavin MT, Cassidy CS, Mar A, Chen FC..  (2001)  Biflavonoids as novel antituberculosis agents.,  11  (16): [PMID:11514148] [10.1016/s0960-894x(01)00382-1]

2. Lin Y, Zembower DE, Flavin MT, Schure RM, Anderson HM, Korba BE, Chen F.  (1997)  Robustaflavone, a naturally occurring biflavanoid, is a potent non-nucleoside inhibitor of hepatitis B virus replication in vitro,  7  (17): [10.1016/S0960-894X(97)00422-8]

3. Lee CW, Choi HJ, Kim HS, Kim DH, Chang IS, Moon HT, Lee SY, Oh WK, Woo ER..  (2008)  Biflavonoids isolated from Selaginella tamariscina regulate the expression of matrix metalloproteinase in human skin fibroblasts.,  16  (2): [PMID:18029185] [10.1016/j.bmc.2007.10.036]

4. Lin YM, Anderson H, Flavin MT, Pai YH, Mata-Greenwood E, Pengsuparp T, Pezzuto JM, Schinazi RF, Hughes SH, Chen FC..  (1997)  In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora.,  60  (9): [PMID:9322359] [10.1021/np9700275]

5. Lin LC, Kuo YC, Chou CJ..  (2000)  Cytotoxic biflavonoids from Selaginella delicatula.,  63  (5): [PMID:10843573] [10.1021/np990538m]

6. Sasaki H, Miki K, Kinoshita K, Koyama K, Juliawaty LD, Achmad SA, Hakim EH, Kaneda M, Takahashi K..  (2010)  beta-Secretase (BACE-1) inhibitory effect of biflavonoids.,  20  (15): [PMID:20598535] [10.1016/j.bmcl.2010.06.021]

7. Aguilar MI, Romero MG, Chávez MI, King-Díaz B, Lotina-Hennsen B..  (2008)  Biflavonoids isolated from Selaginella lepidophylla inhibit photosynthesis in spinach chloroplasts.,  56  (16): [PMID:18646760] [10.1021/jf8010432]

8. Nguyen PH, Ji DJ, Han YR, Choi JS, Rhyu DY, Min BS, Woo MH..  (2015)  Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects.,  23  (13): [PMID:25907369] [10.1016/j.bmc.2015.04.007]

9. Pei Y, Wang C, Yan SF, Liu G..  (2017)  Past, Current, and Future Developments of Therapeutic Agents for Treatment of Chronic Hepatitis B Virus Infection.,  60  (15): [PMID:28383274] [10.1021/acs.jmedchem.6b01442]

10. Ayoub IM, Korinek M, Hwang TL, Chen BH, Chang FR, El-Shazly M, Singab ANB..  (2018)  Probing the Antiallergic and Anti-inflammatory Activity of Biflavonoids and Dihydroflavonols from Dietes bicolor.,  81  (2): [PMID:29381070] [10.1021/acs.jnatprod.7b00476]

11. Wang CG, Yao WN, Zhang B, Hua J, Liang D, Wang HS..  (2018)  Lung cancer and matrix metalloproteinases inhibitors of polyphenols from Selaginella tamariscina with suppression activity of migration.,  28  (14): [PMID:29921475] [10.1016/j.bmcl.2018.06.024]

Source

Source(1):

• Scientific Literature