bilobetin

ID: ALA378188

Chembl Id: CHEMBL378188

Max Phase: Preclinical

Molecular Formula: C31H20O10

Molecular Weight: 552.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bilobetin

Canonical SMILES:  COc1ccc(-c2cc(=O)c3c(O)cc(O)cc3o2)cc1-c1c(O)cc(O)c2c(=O)cc(-c3ccc(O)cc3)oc12

Standard InChI:  InChI=1S/C31H20O10/c1-39-24-7-4-15(26-12-22(37)29-19(34)9-17(33)10-27(29)40-26)8-18(24)28-20(35)11-21(36)30-23(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3

Standard InChI Key:  IWEIJEPIYMAGTH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA378188

   BILOBETIN

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: 552.49

Molecular Weight (Monoisotopic): 552.1056

AlogP: 5.44

#Rotatable Bonds: 4

Polar Surface Area: 170.80

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.09

CX Basic pKa: ┄

CX LogP: 5.23

CX LogD: 3.09

Aromatic Rings: 6

Heavy Atoms: 41

QED Weighted: 0.19

Np Likeness Score: 1.13

References

1. Lee MK, Lim SW, Yang H, Sung SH, Lee HS, Park MJ, Kim YC..  (2006)  Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana.,  16  (11): [PMID:16574412] [10.1016/j.bmcl.2006.03.018]

2. Zeng GZ, Tan NH, Hao XJ, Mu QZ, Li RT..  (2006)  Natural inhibitors targeting osteoclast-mediated bone resorption.,  16  (24): [PMID:17027271] [10.1016/j.bmcl.2006.09.042]

3. Saponara R, Bosisio E..  (1998)  Inhibition of cAMP-phosphodiesterase by biflavones of Ginkgo biloba in rat adipose tissue.,  61  (11): [PMID:9834158] [10.1021/np970569m]

4. 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]

5. Ryu YB, Jeong HJ, Kim JH, Kim YM, Park JY, Kim D, Nguyen TT, Park SJ, Chang JS, Park KH, Rho MC, Lee WS..  (2010)  Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition.,  18  (22): [PMID:20934345] [10.1016/j.bmc.2010.09.035]

6. Wong IL, Chan KF, Chan TH, Chow LM..  (2012)  Flavonoid dimers as novel, potent antileishmanial agents.,  55  (20): [PMID:22989363] [10.1021/jm301172v]

7. Sasaki H, Kitoh Y, Tsukada M, Miki K, Koyama K, Juliawaty LD, Hakim EH, Takahashi K, Kinoshita K..  (2015)  Inhibitory activities of biflavonoids against amyloid-β peptide 42 cytotoxicity in PC-12 cells.,  25  (14): [PMID:26004578] [10.1016/j.bmcl.2015.04.106]

8. 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]

9. Sirimangkalakitti N, Juliawaty LD, Hakim EH, Waliana I, Saito N, Koyama K, Kinoshita K..  (2019)  Naturally occurring biflavonoids with amyloid β aggregation inhibitory activity for development of anti-Alzheimer agents.,  29  (15): [PMID:31138471] [10.1016/j.bmcl.2019.05.020]

10. Xie Y, Zhou X, Li J, Yao XC, Liu WL, Xu PS, Tan GS..  (2022)  Cytotoxic effects of the biflavonoids isolated from Selaginella trichoclada on MCF-7 cells and its potential mechanism.,  56  [PMID:34875389] [10.1016/j.bmcl.2021.128486]

11. Zhang S, Sun Y, Yao F, Li H, Yang Y, Li X, Bai Z, Hu Y, Wang P, Xu X..  (2023)  Ginkgo Biflavones Cause p53 Wild-Type Dependent Cell Death in a Transcription-Independent Manner of p53.,  86  (2.0): [PMID:36700552] [10.1021/acs.jnatprod.2c00959]

Source

Source(1):

• Scientific Literature