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(-)-syringaresinol   Click here for help

GtoPdb Ligand ID: 14312

Synonyms: (-)-Lirioresinol B
Compound class: Natural product
Comment: (-)-Syringaresinol is a phytoestrogen that has been isolated from Zanthoxylum (prickly ash/Sichuan pepper) and other plants. It is reported to exert anti-inflammatory effects [1-3], potentially through estrogenic signalling to the NF-κB pathway [4]. Molecular docking has shown that (-)-syringaresinol may occupy sites within the hydrophobic cores if the ERα and ERβbinding pockets.
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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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 COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3CO[C@@H](C4=CC(=C(C(=C4)OC)O)OC)[C@@H]3CO2
Isomeric SMILES COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3CO[C@H]([C@@H]3CO2)C4=CC(=C(C(=C4)OC)O)OC
InChI InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m1/s1
InChI Key KOWMJRJXZMEZLD-WRMVBYCNSA-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 JJ, Wang TY, Hwang TL. (2008)
Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae.
J Nat Prod, 71 (2): 212-7. [PMID:18211005]
2. Kim KH, Moon E, Choi SU, Kim SY, Lee KR. (2011)
Biological evaluation of phenolic constituents from the trunk of Berberis koreana.
Bioorg Med Chem Lett, 21 (8): 2270-3. [PMID:21420296]
3. Woo KW, Suh WS, Subedi L, Kim SY, Kim A, Lee KR. (2016)
Bioactive lignan derivatives from the stems of Firmiana simplex.
Bioorg Med Chem Lett, 26 (3): 730-733. [PMID:26774654]
4. Zhang L, Jiang X, Zhang J, Gao H, Yang L, Li D, Zhang Q, Wang B, Cui L, Wang X. (2021)
(-)-Syringaresinol suppressed LPS-induced microglia activation via downregulation of NF-κB p65 signaling and interaction with ERβ.
Int Immunopharmacol, 99: 107986. [PMID:34303280]