(5aR,10aS)-2-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one

Base Information

• Chemical Name: (5aR,10aS)-2-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one
• CAS No.: 80651-76-9
• Molecular Formula: C₄₀H₃₆O₁₂
• Molecular Weight: 708.719
• ChEMBL ID: CHEMBL204813
• DSSTox Substance ID: DTXSID20230468
• Metabolomics Workbench ID: 69318,144098
• Nikkaji Number: J47.924A
• Wikidata: Q105326616
• Mol file: 80651-76-9.mol

Synonyms:cathayanon E;sanggenon C;sanggenone C

Chemical Property of (5aR,10aS)-2-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.726
• Boiling Point: 995.5 °C at 760 mmHg
• PKA: 6.61±0.60(Predicted)
• Flash Point: 311.5 °C
• PSA: 214.44000
• Density: 1.512 g/cm³
• LogP: 6.25020
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetone (Slightly), Methanol (Slightly)
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 708.22067658
• Heavy Atom Count: 52
• Complexity: 1430

Purity/Quality:

≥98% ^*data from raw suppliers

Sanggenon C ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(C(C(C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C=C(C=C3)O)O)C4=C(C5=C(C=C4O)OC6(C7=C(C=C(C=C7)O)OC6(C5=O)O)CC=C(C)C)O
• Isomeric SMILES: CC1=C[C@@H]([C@@H]([C@H](C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C=C(C=C3)O)O)C4=C(C5=C(C=C4O)O[C@@]6(C7=C(C=C(C=C7)O)O[C@@]6(C5=O)O)CC=C(C)C)O
• Description: Sanggenone C is a flavonoid that has been found in mulberry bark and has diverse biological activities. It inhibits TNF-α- or IL-1β-induced polymorphonuclear leukocyte (PMN) adhesion to human synovial cells (HSCs; IC50s = 27.29 and 54.43 nM, respectively), as well as inhibits NF-κB activation in HSCs. Sanggenone C induces apoptosis and production of reactive oxygen species (ROS) in HT-29 cells when used at concentrations ranging from 10 to 40 μM. It decreases cell viability of HT-29 cells in vitro and reduces tumor growth in an HT-29 mouse xenograft model when administered at a dose of 10 mg/kg. Sanggenone C increases vertebrate column bone mineralization in a zebrafish model of prednisone-induced osteoporosis. It also attenuates cardiac hypertrophy and fibrosis and reduces activation of nuclear factor of activated T cells 2 (NFAT2) in a mouse model of pressure overload-induced cardiac hypertrophy.
• Uses: Sanggenone C is a flavanone isolated from Morus plant that showed cytotoxicity against human oral tumor cell lines (HSC-2 and HSG). Sanggenone C is also an inhibitor of protein tyrosine phosphatase 1B.