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fangchinoline   Click here for help

GtoPdb Ligand ID: 14520

Synonyms: 7-O-demethyltetrandrine | Hanfangichin B | Tetrandrine B
Immunopharmacology Ligand
Compound class: Natural product
Comment: Fangchinoline is an alkaloid constituent that has been isolated from the tuberous roots of the Botryodiscia (formerly Stephania) tetrandra S. Moore plant [5,11]. Anti-inflammatory, anti-tumour , anti-oxidant and anti-viral activities have been reported [1,4,6-10,12-15].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 72.86
Molecular weight 608.72
XLogP 2.68
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CCC2=C3C=C(C(=C2)OC)OC4=C(C(=CC5=C4[C@H](CC6=CC=C(C(=C6)OC7=CC=C(C=C7)C[C@@H]31)OC)N(C)CC5)OC)O
Isomeric SMILES CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
InChI InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m0/s1
InChI Key IIQSJHUEZBTSAT-VMPREFPWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Chen J, Hu J, He J, Zhang B, Tan H, Wang Q, Hu H, Xu S, Tan CSH, Zhang J et al.. (2025)
Fangchinoline suppresses melanoma metastasis by inducing senescence of circulating tumor cells.
Biomed Pharmacother, 193: 118770. [PMID:41242135]
2. Chen X, Hong F, Wu H, Shen Y, Xia H, Xu R, Shi L. (2024)
Effects of baicalein and fangchinoline on abemaciclib metabolism in vivo and in vitro and molecular docking analysis.
Arabian J of Chemistry, 18: 106073. DOI: 10.1016/j.arabjc.2024.106073
3. Choi HS, Kim HS, Min KR, Kim Y, Lim HK, Chang YK, Chung MW. (2000)
Anti-inflammatory effects of fangchinoline and tetrandrine.
J Ethnopharmacol, 69 (2): 173-9. [PMID:10687873]
4. He W, Li X, Ding Q, Zhang T, Zheng J, Lu X, Li J, Jin C, Xu Y. (2025)
Fangchinoline alleviates the progression of osteoarthritis through the nuclear factor kappa B signaling pathway.
Toxicol Appl Pharmacol, 496: 117241. [PMID:39894170]
5. Huang KC. (1999)
Fang Ji.  In  The pharmacology of Chinese herbs (CRC press) 141. [ISBN:0849316650]
6. Li B, Qiao L, Li X, Yang G, Wang K, Wang H, Wu S, Yan H, Jiang J, Li Y. (2025)
Bisbenzylisoquinoline alkaloids inhibit influenza virus replication by disrupting endosomal acidification.
Virol J, 22 (1): 181. [PMID:40468427]
7. Liu Y, Wang Y, Wang J, Wang X, Chen L, Han T, Lian H, Gan M, Wang J. (2024)
Fangchinoline suppresses hepatocellular carcinoma by regulating ROS accumulation via the TRIM7/Nrf2 signaling pathway.
Phytomedicine, 135: 156143. [PMID:39461200]
8. Pocasap P, Kaimuangpak K, Phukmee K, Prawan A, Kongpetch S, Senggunprai L. (2025)
Unveiling the Anticancer Potential and Molecular Mechanisms of Fangchinoline Against Cholangiocarcinoma Using FTIR Microspectroscopy, In Vitro and In Silico Approaches.
Integr Cancer Ther, 24: 15347354251396513. [PMID:41261767]
9. Satria D, Hasibuan PAZ, Masfria M, Waruwu SB, Yeun-Mun C, Hermanto FE, Widodo N. (2026)
In silico approach and in vitro study of fangchinoline-induced apoptosis and reactive oxygen species production in HER2-overexpressing breast cancer cells.
Contemp Oncol (Pozn), 30 (1): 56-67. [PMID:42089032]
10. Wang J, Xie F, Jia X, Wang X, Kong L, Li Y, Liang X, Zhang M, He Y, Feng W et al.. (2024)
Fangchinoline induces antiviral response by suppressing STING degradation.
J Pharm Anal, 14 (6): 100972. [PMID:39027910]
11. Wang Y, Cao B, Shi S, Gao S, Ge D. (2025)
Supramolecular solvent-based ultrasound-assisted extraction of fangchinoline and tetrandrine from the roots of Stephaniae tetrandrae.
Anal Methods, 17 (23): 4745-4752. [PMID:40421645]
12. Xie J, Shi Z, Sun L, Wu Y, Feng J, Wang H, Lai H. (2025)
Fangchinoline suppresses nasopharyngeal carcinoma progression by inhibiting SQLE to regulate the PI3K/AKT pathway dysregulation.
Phytomedicine, 140: 156484. [PMID:40090046]
13. Yang S, Yang X, Wang Z, Li W, Cao R, Zhong W. (2024)
Fangchinoline Inhibits Zika Virus by Disrupting Virus Internalization.
ACS Infect Dis, 10 (12): 4066-4072. [PMID:39534987]
14. Yin H, Lian H, Wang Y, Chen L, Liu X, Liu Y. (2025)
Fangchinoline attenuates hepatic fibrosis by regulating taurine metabolism and oxidative stress.
Front Pharmacol, 16: 1633519. [PMID:40910002]
15. Zheng Y, Ling M, Feng J, Yu Y, Song M, Tao Y, Zhang A, Wang X. (2025)
Inhibition of PRRSV replication by fangchinoline and cepharanthine from medicinal herbs through targeting of the CD163 protein.
Vet Microbiol, 306: 110536. [PMID:40349495]