(3Z,5R,6R,14aS)-6-(Acetyloxy)-3-ethylidene-3,4,5,6,14,14a-hexahydro-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7,13(9H)-trione
Basic information
- CAS
64191-69-1- Standard SMILES
C/C=C1/C[C@@H](C)[C@@](C)(OC(C)=O)C(=O)OCc2ccn3c2[C@H](CC3=O)OC1=O- InChIKey
NTGIQQBAUYBEBF-ZCXFZNNUSA-N- Molecular formula
- C20H23NO7
- Average molar mass
- 389.4 g/mol
- Monoisotopic mass
- 389.14745207
Overview
Senaetnine is a member of pyrrolizines.
Names & identifiers
- Preferred name
- (3Z,5R,6R,14aS)-6-(Acetyloxy)-3-ethylidene-3,4,5,6,14,14a-hexahydro-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7,13(9H)-trione
- IUPAC
- [(1S,4Z,6R,7R)-4-ethylidene-6,7-dimethyl-3,8,15-trioxo-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadeca-11(17),12-dien-7-yl] acetate
- English name
- senaetnine
- Molecular formula
- C20H23NO7
- Molecular weight
- 389.4
Names & synonyms
Senaetnine64191-69-1DTXSID201100988((1S,4Z,6R,7R)-4-ethylidene-6,7-dimethyl-3,8,15-trioxo-2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadeca-11(17),12-dien-7-yl) acetate(3Z,5R,6R,14aS)-6-(Acetyloxy)-3-ethylidene-3,4,5,6,14,14a-hexahydro-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7,13(9H)-trione(3Z,5R,6R,14aS)-6-(Acetyloxy)-3-ethylidene-3,4,5,6,14,14a-hexahydro-5,6-dimethyl[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7,13(9H)-trione[(1S,4Z,6R,7R)-4-Ethylidene-6,7-dimethyl-3,8,15-trioxo-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadeca-11(17),12-dien-7-yl] acetateRefChem:906083Senecionan-5,11,16-trione, 12-(acetyloxy)-3,8-didehydro-, (7beta)-DTXCID201532690((1S,7R,8R)-7-((Z)-2-methylbut-2-enoyl)oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl)methyl (Z)-2-(hydroxymethyl)but-2-enoateC10386
Show more names
Senaetnin[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7,13(9H)-trione, 6-(acetyloxy)-3-ethylidene-3,4,5,6,14,14a-hexahydro-5,6-dimethyl-, (3Z,5R,6R,14aS)-
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 730
Physicochemical properties
- Boiling point
- 627.2 · 627.2±55.0 °C(Predicted)
- Density
- 1.34 · 1.34±0.1 g/cm3(Predicted)
- pka
- -8.3 · -8.30±0.60(Predicted)
Chemistry & industry
Applications
OccurrenceSenaetnine has been obtained from an unclassified species of Senecio. It crystallizes as colourless needles from Et20-light petroleum and has the following optical rotations:-[α]D +10.6°, lams +11.10, [α]D +12.6°, [α]D +13.1°, [α]D +31.5° (c 2.5, CHCl3).
Additional notes
DefinitionChEBI: Senaetnine is a member of pyrrolizines.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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