Evonimine, 8-(acetyloxy)-O(sup 2)-benzoyl-O(sup 2)-deacetyl-8-deoxo-, (8-alpha)-
Basic information
- CAS
11088-09-8- Standard SMILES
CC(=O)OC[C@]12[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]3[C@@H](OC(C)=O)[C@@]14O[C@@]3(C)COC(=O)c1cccnc1CC[C@H](C)C(=O)O[C@@H]([C@H](OC(=O)c1ccccc1)[C@@H]2OC(C)=O)C4(C)O- InChIKey
ZOCKGJZEUVPPPI-FZILPIMGSA-N- Molecular formula
- C43H49NO18
- Average molar mass
- 867.8 g/mol
- Monoisotopic mass
- 867.29496371
Names & identifiers
- Preferred name
- Evonimine, 8-(acetyloxy)-O(sup 2)-benzoyl-O(sup 2)-deacetyl-8-deoxo-, (8-alpha)-
- IUPAC
- [(1S,3R,15S,18S,19R,20R,21R,22S,23R,24R,25R)-20,22,23,25-tetraacetyloxy-21-(acetyloxymethyl)-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-19-yl] benzoate
- English name
- WILFORINE
- Molecular formula
- C43H49NO18
- Molecular weight
- 867.85
Names & synonyms
BRN 00781568,11-Epoxy-9,12-ethano-11,15-methano-5H,11H-[1,9]dioxacyclooctadecino[4,3-b]pyridine-5,17(18H)-dione, 10,13,22,23-tetrakis(acetyloxy)-12-[(acetyloxy)methyl]-14-(benzoyloxy)-7,8,9,10,12,13,14,15,19,20-decahydro-21-hydroxy-8,18,21-trimethyl-, (8R,9R,10R,11S,12S,13R,14R,15S,18S,21S,22S,23R)-AKOS032948279Evonimine, 8-(acetyloxy)-O(sup 2)-benzoyl-O(sup 2)-deacetyl-8-deoxo-, (8-alpha)-[(1S,3R,15S,18S,19R,20R,21R,22S,23R,24R,25R)-20,22,23,25-tetraacetyloxy-21-(acetyloxymethyl)-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-19-yl] benzoateWILFORINEWilforine-RM26-DeoxywilfordineWilforine (Standard)Wilforine, 10 mM in DMSO(8α)-8-(Acetyloxy)-2-O-benzoyl-2-O-deacetyl-8-deoxoevonimineEvonimine, 8-(acetyloxy)-O2-benzoyl-O2-deacetyl-8-deoxo-, (8α)-
Show more names
(8R,9R,10R,11S,12S,13R,14R,15S,18S,21S,22S,23R)-10,13,22,23-Tetrakis(acetyloxy)-12-[(acetyloxy)methyl]-14-(benzoyloxy)-7,8,9,10,12,13,14,15,19,20-decahydro-21-hydroxy-8,18,21-trimethyl-8,11-epoxy-9,12-ethano-11,15-m
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 253 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 19
- Rotatable bonds
- 14
- Heavy atoms
- 62
- Formal charge
- 0
- Complexity
- 1,800
Physicochemical properties
- Melting point
- 158 · 158-163℃
- Boiling point
- 871.5 · 871.5±65.0 °C(Predicted)
- Density
- 1.41 · 1.41
- solubility
- Soluble in methan
- form
- powder
- pka
- 11.7 · 11.70±0.70(Predicted)
- color
- White-yellowish
- InChIKey
- ZOCKGJZEUVPPPI-UHFFFAOYSA-N
- SMILES
- C(C12C(C(OC(C3C=CC=CC=3)=O)C3OC(C(CCC4=NC=CC=C4C(=O)OCC4(C)C(C(OC(=O)C)C1OC(=O)C)C(OC(=O)C)C2(C3(O)C)O4)C)=O)OC(=O)C)OC(=O)C
- FDA UNII
- 8 YV57M7EYI · 8YV57M7EYI
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H311-H331
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: 418mg/kg
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
- Toxicity
- LD50 intraperitoneal in mouse: 418mg/kg
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301-H311-H331
- Precautionary statements
- P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Chemistry & industry
Applications
DescriptionPresent in Tripterygiurn wilfordii Hook, this base forms colourless plates when crystallized from MeOH-Me2CO. It has [α]25/sup>D + 30° (Me2CO).
UsesWilforine is a major bioactive sesquiterpene alkaloid extracted from Tripterygium wifordii Hook F. displaying anti-inflammatory activity.
Additional notes
DefinitionChEBI: An organic heteropentacyclic compound and pyridine alkaloid with formula C43H49NO18 originally isolated from the roots of Tripterygium wilfordii.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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