(9R,10R)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo(10.7.0.0^(2,7).0^(14,18))nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-9-ol
Basic information
- CAS
58546-54-6- Standard SMILES
COc1cc2c(c(OC)c1OC)-c1c(cc3c(c1OC)OCO3)C[C@@H](C)[C@](C)(O)C2- InChIKey
ZWRRJEICIPUPHZ-SFDCACGMSA-N- Molecular formula
- C23H28O7
- Average molar mass
- 416.5 g/mol
- Monoisotopic mass
- 416.18350323
Overview
Besigomsin is a tannin.
Names & identifiers
- Preferred name
- (9R,10R)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo(10.7.0.0^(2,7).0^(14,18))nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-9-ol
- IUPAC
- (9R,10R)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-9-ol
- English name
- Gomisin A
- Molecular formula
- C23H28O7
- Molecular weight
- 416.47
Names & synonyms
RefChem:1050757(9R,10R)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo(10.7.0.0^(2,7).0^(14,18))nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-9-olNCGC00181777-01Schisandrol-BCAS-58546-54-6NCGC00183134-01Besigomsin (JAN/INN)SCHEMBL2701466CHEMBL1834755CHEBI:31272ZWRRJEICIPUPHZ-SFDCACGMSA-NTox21_113370
Show more names
SCHISANDROL BTJN-101GOMISIN ABesigomsinBESIGOMISINwuweizichunbSCHIZANDROL BwuweizialcoholbGrifola frondsa
Tox21_113433PD014436NS00127380D01752(6R,7R)-1,2,3,13-Tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydro-11H-benzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxol-6-ol
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 75.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 588
Physicochemical properties
- Melting point
- 88.5 °C · 88.5°C
- Boiling point
- 454.79 °C · 454.79°C (rough estimate)
- Density
- 1.1772 · 1.1772 (rough estimate)
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 50 mg/mL · DMSO : 50 mg/mL (120.06 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
- form
- powder to crystal
- pka
- 14.58 · 14.58±0.40(Predicted)
- color
- White to Light yellow
- biological source
- Schisandra chinensis
- InChI
- 1S/C23H28O7/c1-12-7-13-8-16-20(30-11-29-16)22(28-6)17(13)18-14(10-23(12,2)24)9-15(25-3)19(26-4)21(18)27-5/h8-9,12,24H,7,10-11H2,1-6H3/t12-,23-/m0/s1
- InChIKey
- ZWRRJEICIPUPHZ-MYODQAERSA-N
- SMILES
- C[C@]1([H])[C@@](C)(O)CC2=C(C(OC)=C(OC)C(OC)=C2)C3=C(OC)C4=C(OCO4)C=C3C1
- LogP
- 4.77 · 4.770 (est)
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
- hs_code
- 29329990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Precautionary statements
- P501-P270-P264-P301+P312+P330
Chemistry & industry
Applications
DescriptionSchisandrol B is a lignan originally isolated from S. chinensis that has hepatoprotective activity. It increases the expression of pregnane X receptor (PXR) target genes involved in bile acid metabolism, including Cyp3a11, Ugt1a1, Oatp2, and Mrp3 in mouse liver and CYP3A4, UGT1A1, and OATP2 in HEK293T cells. It also protects against lithocholic acid-induced hepatic necrosis and intrahepatic cholestasis in wild-type, but not Pxr-null, mice and decreases mortality in a mouse model of cholestasis when administered at a dose of 100 mg/kg twice per day. It also promotes liver regeneration following partial hepatectomy and protects against hepatotoxicity induced by acetaminophen .
UsesSchizandrol B exhibits potent protective effects of on ET-1-induced dysfunctional human-induced pluripotent stem cell-derived cardiomyocytes (hiPS-CMs). Anti-cholestasis effect.
Related reactions
0 records
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Compound notes
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