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schisandrin A   Click here for help

GtoPdb Ligand ID: 2769

Synonyms: (-)-deoxyschisandrin | (-)-dimethylgomisin J | deoxyschizandrin | schizandrin-A
Compound class: Natural product
Comment: Schisandrin A is a lignan derived from the fruiting bodies of the Schisandra chinensis vine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 55.38
Molecular weight 416.22
XLogP 5.66
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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Canonical SMILES COc1c2c(CC(C)C(Cc3c2c(OC)c(c(c3)OC)OC)C)cc(c1OC)OC
Isomeric SMILES COc1c2c(C[C@H](C)[C@@H](Cc3c2c(OC)c(c(c3)OC)OC)C)cc(c1OC)OC
InChI InChI=1S/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14+
InChI Key JEJFTTRHGBKKEI-OKILXGFUSA-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. Li WL, Xin HW, Su MW, Xiong L. (2010)
Inhibitory effects of schisandrin A and schisandrin B on CYP3A activity.
Methods Find Exp Clin Pharmacol, 32 (3): 163-9. [PMID:20448858]
2. Mu Y, Zhang J, Zhang S, Zhou HH, Toma D, Ren S, Huang L, Yaramus M, Baum A, Venkataramanan R, Xie W. (2006)
Traditional Chinese medicines Wu Wei Zi (Schisandra chinensis Baill) and Gan Cao (Glycyrrhiza uralensis Fisch) activate pregnane X receptor and increase warfarin clearance in rats.
J Pharmacol Exp Ther, 316 (3): 1369-77. [PMID:16267138]
3. Qin XL, Chen X, Wang Y, Xue XP, Wang Y, Li JL, Wang XD, Zhong GP, Wang CX, Yang H et al.. (2014)
In vivo to in vitro effects of six bioactive lignans of Wuzhi tablet (Schisandra sphenanthera extract) on the CYP3A/P-glycoprotein-mediated absorption and metabolism of tacrolimus.
Drug Metab Dispos, 42 (1): 193-9. [PMID:24195812]
4. Wu J, Cao Y, Zhang Y, Liu Y, Hong JY, Zhu L, Ge G, Yang L. (2014)
Deoxyschizandrin, a naturally occurring lignan, is a specific probe substrate of human cytochrome P450 3A.
Drug Metab Dispos, 42 (1): 94-104. [PMID:24131672]