Silidianin, INN
Basic information
- CAS
29782-68-1- Standard SMILES
COc1cc(C2C3CC(C4Oc5cc(O)cc(O)c5C(=O)C4O)C4C2COC4(O)C3=O)ccc1O- InChIKey
RYFSLTQGWPBSRH-UHFFFAOYSA-N- Molecular formula
- C25H24O10
- Average molar mass
- 484.5 g/mol
- Monoisotopic mass
- 484.13694696
Overview
Silidianin is a member of flavanones.
Names & identifiers
- Preferred name
- Silidianin, INN
- IUPAC
- 3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-(3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl)-4-oxatricyclo[4.3.1.03,7]decan-2-one
- English name
- Silydianin
- Molecular formula
- C25H22O10
- Molecular weight
- 482.44
Names & synonyms
Silidianin, INNSilybum substance E5CHEBI:1781843-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-(3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl)-4-oxatricyclo[4.3.1.03,7]decan-2-oneSILIDIANINSILYDIANINSilydianin-RMSILYDIANIN(P)Silydianin，SDSILYDIANIN hplcSilydianin (20 mg)SILYDIANIN USP/EP/BP
Show more names
Silydianin (Standard)Silydianin, 10 mM in DMSO
Database identifiers
- CAS
29782-68-1- PubChem CID
- 45934367
- ChEBI
CHEBI:178184
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 3
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 880
Experimental & physicochemical properties
Melting Point191 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 191 ℃ · 191℃
- Boiling point
- 819 · 819.0±65.0 °C(Predicted)
- Density
- 1.675 · 1.675±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Sonicated)
- form
- Solid
- pka
- 7.41 · 7.41±0.60(Predicted)
- color
- White to Off-White
- Water Solubility
- practically insoluble in water
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- CYGIJEJDYJOUAN-JSGXPVSSSA-N
- SMILES
- COc1cc(ccc1O)[C@@H]2[C@H]3CO[C@]4(O)[C@H]3C(=C[C@H]2C4=O)[C@H]5Oc6cc(O)cc(O)c6C(=O)[C@@H]5O
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
- 3
- hs_code
- 2932996560
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionSilydianin is a flavonolignan found in S. marianum and has diverse biological activities. It inhibits tyrosinase (IC50 = 2.6 μM for the mushroom enzyme) and scavenges DPPH radicals in a cell-free assay (IC50 = 66.8 μM). Silydianin (100 μM) protects against cytotoxicity induced by allyl alcohol, carbon tetrachloride, paracetamol (acetaminophen), or D-galactosamine in primary human hepatocytes. It inhibits the proliferation of DU145 and PC3 prostate cancer cells when used at a concentration of 90 μM. Silydianin (1%) prevents methacholine-induced airway hyperresponsiveness (AHR) and reduces blood and bronchoalveolar lavage fluid (BALF) levels of eosinophils in an ovalbumin-sensitized mouse model of allergic asthma when administered via inhalation.
UsesSilydianin is an active constituent of Silybium marianum and is known the exhibit anti-inflammatory activity which regulates caspase-3 activation which affects cell membranes and acts as a free radical scavenger.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…