Schisandrin derivative
Basic information
- CAS
61301-33-5- Standard SMILES
COc1c2c(cc3c1-c1c(cc4c(c1OC)OCO4)CC(C)C(C)C3)OCO2- InChIKey
HTBWBWWADZJXID-UHFFFAOYSA-N- Molecular formula
- C22H24O6
- Average molar mass
- 384.4 g/mol
- Monoisotopic mass
- 384.15728848
Overview
schisandrin C has been reported in Schisandra sphenanthera and Schisandra chinensis with data available.
Names & identifiers
- Preferred name
- Schisandrin derivative
- IUPAC
- 3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.02,10.04,8.017,21]docosa-1(22),2,4(8),9,15,17(21)-hexaene
- English name
- WUWEIZISU C
- Molecular formula
- C22H24O6
- Molecular weight
- 384.42
Names & synonyms
Schisandrin derivativeNSC609258Schizandrin-C;Wuweizisu-CMFCD0027217066138-32-7Schisandrin dervativeR-(+)-Wuweizisu CSchisandrin C [M+H]+orb3171757SCHEMBL12280310Schisandrin C, >=98% (HPLC)CCG-268455
Show more names
SCHIZANDRIN CWUWEIZISU C,8-dimethyl-Schizandrin C-RM(S)-(-)-Schisandrin CWUWEIZISU C USP/EP/BPSchisandrin C (Standard)Schisandrin C >=98% (HPLC)Schisandrin C (Schizandrin-CSchisandrin C, 10 mM in DMSO
EBC-615468NSC-609258NCGC00385072-01AC-34835DA-67487LS-14945T129700[1,3]Dioxolo[4'',5'']benzo[1'',2'':3',4']cycloocta[1',2':4,5]benzo[1,2-d]-1,3-dioxole, 5,6,7,8-tetrahydro-13,14-dimethoxy-6,7-dimethyl-
Database identifiers
- CAS
61301-33-5
Properties
Computed structural properties
- XLogP
- 5
- Topological polar surface area
- 55.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 509
Physicochemical properties
- Melting point
- 122 · 122-123℃
- Boiling point
- 549.2 · 549.2±50.0 °C(Predicted)
- Density
- 1.232 · 1.232
- storage temp.
- 2 · 2-8°C
- solubility
- 8.33 mg/mL · DMSO : 8.33 mg/mL (21.67 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
- form
- powder
- color
- White
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- 1S/C22H24O6/c1-11-5-13-7-15-19(27-9-25-15)21(23-3)17(13)18-14(6-12(11)2)8-16-20(22(18)24-4)28-10-26-16/h7-8,11-12H,5-6,9-10H2,1-4H3
- InChIKey
- HTBWBWWADZJXID-UHFFFAOYSA-N
- SMILES
- COC1=C2C(OCO2)=CC3=C1C(C(OC)=C(OCO4)C4=C5)=C5CC(C)C(C)C3
- LogP
- 5.623 · 5.623 (est)
- FDA UNII
- 8754 W6B3G · C8754W6B3G
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H410
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P273-P391-P501
Chemistry & industry
Applications
DescriptionSchisandrin C is a lignan originally isolated from Schizandrae that has diverse biological activities. It decreases viability of U937 cells in a concentration-dependent manner and induces cell cycle arrest at the G1 phase when used at a concentration of 100 μM. Schisandrin C (5-20 μM) decreases hydrogen peroxide-induced cell death and production of reactive oxygen species (ROS) in C2C12 skeletal muscle cells. It also decreases levels of matrix metalloproteinase-2 (MMP-2), MMP-9, COX-2, VCAM-1, IL-1β, and TNF-α in hydrogen peroxide-stimulated C2C12 cells. Schisandrin C decreases lipoteichoic acid-induced production of nitric oxide (NO), prostaglandin E2 (PGE2; ), TNF-α, IL-1β, and IL-6 in mouse primary microglia. In vivo, schisandrin C (200 mg/kg) decreases serum alanine amino transferase (ALT) and aspartate amino transferase (AST) activity, increases hepatic mitochondrial and total glutathione (GSH) levels, and reduces liver injury in a mouse model of acetaminophen-induced liver injury partially via inhibition of the cytochrome P450 (CYP) isoforms CYP2E1, CYP1A2, and CYP3A11.
UsesSchisandrin C potently inhibits proprotein convertase subtillsin-kexin type 9 (PCSK9) mRNA expression. Also, it displays strong protective effects in SH-SY5Y cells against serum and glucose deprivation (SGD) injury.
Related reactions
0 records
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Compound notes
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