methyl (1S,2S)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.03,11.05,10]octadeca-3(11),5,7,9-tetraene-2-carboxylate
Basic information
- CAS
10012-73-4- Standard SMILES
CC=C1CN2CCc3c([nH]c4ccccc34)[C@@](CO)(C(=O)OC)[C@H]1CC2- InChIKey
MBXJCHZRHROMQA-UWJYYQICSA-N- Molecular formula
- C21H26N2O3
- Average molar mass
- 354.4 g/mol
- Monoisotopic mass
- 354.1943427
Overview
CID 443367 has been reported in Rauvolfia serpentina, Tabernaemontana cymosa, and other organisms with data available.
Names & identifiers
- Preferred name
- methyl (1S,2S)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.03,11.05,10]octadeca-3(11),5,7,9-tetraene-2-carboxylate
- IUPAC
- methyl (1S,2S)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.03,11.05,10]octadeca-3(11),5,7,9-tetraene-2-carboxylate
- English name
- stemmadenine
- Molecular formula
- C21H26N2O3
- Molecular weight
- 354.44
Names & synonyms
10012-73-4DTXSID70905215Methyl (6S,7S)-5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylateMethyl 5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylatestemmadenine15-epi-Stemmadenine(19E)-2,7,19,20-Tetradehydro-17-hydroxy-3,7-secocuran-16-carboxylic acid methyl ester(15β,19E)-2,7,19,20-Tetradehydro-17-hydroxy-3,7-secocuran-16-carboxylic acid methyl ester1H-3,6-Ethanoazonino[5,4-b]indole-7-carboxylic acid, 5-ethylidene-2,4,5,6,7,8-hexahydro-7-(hydroxymethyl)-, methyl ester, (3S,5E,6S,7S)-
Database identifiers
- CAS
10012-73-4- PubChem CID
- 443367
- DTXSID
DTXSID70905215
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 65.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 578
Physicochemical properties
- Melting point
- 189 · 189-193°C
- Boiling point
- 518.5 · 518.5±50.0 °C(Predicted)
- Density
- 1.27 · 1.27±0.1 g/cm3(Predicted)
- pka
- 14.81 · 14.81±0.10(Predicted)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 RBX39D6AB · 7RBX39D6AB
Chemistry & industry
Applications
DescriptionFirst isolated from various species of Stemmadenia, this alkaloid has subsequently been found in DipZorrhynchus rondyZocarpon subsp. mossambiensis Benth. and MeZodinus australis. The following specific rotations have been reported; [α]19D + 310° (c 0.527, pyridine), [α]20D~O + 329° (pyridine) and [α]25D~S + 324° (pyridine). The alkaloid gives an ultraviolet spectrum exhibiting absorption maxima at 227, 284 and 292 m/J. with shoulders at 275 and 305 m/J.. One nitrogen atom is tertiary, the other being part of the indole ring. The solution in concentrated HN03 is a bright yellow.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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