3,6,9-Trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-8-yl hexopyranoside
Basic information
- CAS
57576-33-7- Standard SMILES
C=C1C(=O)OC2C1CCC(=C)C1CC(OC3OC(CO)C(O)C(O)C3O)C(=C)C12- InChIKey
OIOLZODVFMMERF-UHFFFAOYSA-N- Molecular formula
- C21H28O8
- Average molar mass
- 408.4 g/mol
- Monoisotopic mass
- 408.17841785
Overview
3,6,9-Trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-8-yl hexopyranoside has been reported in Ainsliaea fragrans, Crepis sibirica, and other organisms with data available.
Names & identifiers
- Preferred name
- 3,6,9-Trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-8-yl hexopyranoside
- IUPAC
- 3,6,9-trimethylidene-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
- English name
- (3aS)-3a,4,5,6,6aβ,7,8,9,9aβ,9bα-Decahydro-8α-(β-D-glucopyranosyloxy)-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one
- Molecular formula
- C21H28O8
- Molecular weight
- 408.44
Names & synonyms
DTXSID90973153NSC2745383,6,9-Trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-8-yl hexopyranosideAzuleno[4, 8-(.beta.-D-glucopyranosyloxy)decahydro-3,6,9-tris(methylene)-, [3aS-(3a.alpha.,6a.alpha.,8.beta.,9a.alpha.,9b.beta.)]-VernoflexuosideAzuleno[4,5-b]furan-2(3H)-one, 8-(β-D-glucopyranosyloxy)decahydro-3,6,9-tris(methylene)-, (3aS,6aR,8S,9aR,9bS)-(3aS)-3a,4,5,6,6aβ,7,8,9,9aβ,9bα-Decahydro-8α-(β-D-glucopyranosyloxy)-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one
Database identifiers
- CAS
57576-33-7- PubChem CID
- 321680
- DTXSID
DTXSID90973153
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 126 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 732
Physicochemical properties
- FDA UNII
- 56 HA3QTL3C · 56HA3QTL3C
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
UsesGlucozaluzanin C is a lignan isolated from the MeOH extract of the roots of Ainsliaea acerifolia (Compositae). Glucozaluzanin C has ED50 value of 2.45 μg/mL, 1.37μg/mL, 0.40 μg/mL, 1.41 μg/mL, 1.43 μg/mL for A549 cells, SK-OV-3 cells, SK-MEL-2 cells, XF498 cells, HCT15 cells, respectively[1].
Additional notes
DefinitionChEBI: Vernoflexuoside is a sesquiterpene lactone.
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