Structure Database (LMSD)

Common Name
Sciadopitysin
Systematic Name
Synonyms
LM ID
LMPK12040006
Formula
Exact Mass
Calculate m/z
580.13695
Status
Curated


Classification

Biological Context

Sciadopitysin is a biflavonoid originally isolated from G. biloba and has diverse biological activities.1,2,3,4 It reduces cytotoxicity induced by amyloid-β (1-42) (Aβ42) in PC12 cells (EC50 = 9.84 μM).2 Sciadopitysin (0.1-10 μM) decreases methylglyoxal-induced insulin secretion, production of reactive oxygen species (ROS), cardiolipin peroxidation, and cytotoxicity in RIN-m5F pancreatic β-cells.3 It inhibits P-glycoprotein (P-gp; IC50 = 53.42 μM) and increases cellular toxicity of paraquat and paclitaxel in MDR1-MDCKII cells.5 Sciadopitysin inhibits RANKL-induced mRNA expression of the osteoclast-specific genes CTSK, TRAP, and MMP-9, activation of NF-κB, and osteoclastogenesis in a mouse model of LPS-induced bone loss.4

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ginkgo biloba (#3311)
Ginkgoopsida (#29811)
Flavonoids of Ginkgo biloba,
Ginkgo Biloba A Global Treasure, 1997

String Representations

InChiKey (Click to copy)
YCXRBCHEOFVYEN-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C33H24O10/c1-39-18-7-4-16(5-8-18)27-15-25(38)32-23(36)13-22(35)30(33(32)43-27)20-10-17(6-9-26(20)41-3)28-14-24(37)31-21(34)11-19(40-2)12-29(31)42-28/h4-15,34-36H,1-3H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(OC)=C(C4=C(O)C=C(O)C5C(=O)C=C(C6=CC=C(OC)C=C6)OC4=5)C=3)=CC(=O)C=2C(O)=C1

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 43
Rings 6
Aromatic Rings 6
Rotatable Bonds 6
Van der Waals Molecular Volume 485.56
Topological Polar Surface Area 148.80
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 10
logP 7.84
Molar Refractivity 159.70

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Created at
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Updated at
8th Jun 2021