6-Benzoylheteratisine
Basic information
- CAS
99759-48-5- Standard SMILES
CCN1C[C@]2(C)CC[C@H](OC)C34C5C[C@@H]6CC[C@@](O)(C5C(=O)O6)C(C13)[C@@H](OC(=O)c1ccccc1)[C@@H]42- InChIKey
XVVZJDDPRFFKTQ-UPWHZOCASA-N- Molecular formula
- C29H37NO6
- Average molar mass
- 495.6 g/mol
- Monoisotopic mass
- 495.2620879
Overview
an Aconitum alkaloid
Names & identifiers
- Preferred name
- 6-Benzoylheteratisine
- IUPAC
- [(6S,9S,14R,17S,18R,19S)-12-ethyl-9-hydroxy-17-methoxy-14-methyl-4-oxo-5-oxa-12-azahexacyclo[8.7.2.12,6.01,11.03,9.014,18]icosan-19-yl] benzoate
- English name
- Heteratisan-14-one, 6-(benzoyloxy)-20-ethyl-8-hydroxy-1-methoxy-4-meth yl-, (1alpha,6beta)-
- Molecular formula
- C29H37NO6
- Molecular weight
- 495.61
Names & synonyms
6-Benzoylheteratisine6-benzoyl-heteratisineRefChem:913838Heteratisine 6-benzoate6-O-BenzoylheteratisineHeteratisan-14-one, 6-(benzoyloxy)-20-ethyl-8-hydroxy-1-methoxy-4-methyl-, (1alpha,6beta)-8H-13,3,6a-Ethanylylidene-7,10-methanooxepino(3,4-i)-1-benzazocin-8-one, tetradecahydro-14-(benzoyloxy)-1-ethyl-12a-hydroxy-6-methoxy-3-methyl-, (3R-(3-alpha,6-beta,6a-alpha,7-beta,7a-alpha,10-beta,12a-alpha,13-alpha,13a-beta,14S*,15R*))-Heteratisan-14-one, 6-(benzoyloxy)-2-o-ethyl-8-hydroxy-1-methoxy-4-methyl-, (1-alpha,6-beta)-O-benzoylheteratisineHeteratisan-14-one, 6-(benzoyloxy)-20-ethyl-8-hydroxy-1-methoxy-4-methHeteratisan-14-one, 6-(benzoyloxy)-20-ethyl-8-hydroxy-1-methoxy-4-meth yl-, (1alpha,6beta)-Inhibitor,6Benzoylheteratisine,Sodium Channel,inhibit,6-Benzoylheteratisine,Na+ channels,Na channels,6 Benzoylheteratisine
Show more names
8H-13,3,6a-Ethanylylidene-7,10-methanooxepino[3,4-i]-1-benzazocin-8-one, 14-(benzoyloxy)-1-ethyltetradecahydro-12a-hydroxy-6-methoxy-3-methyl-, (3R,6S,6aS,7R,7aS,10S,12aS,13R,13aR,14S,15R)-
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 85.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 950
Physicochemical properties
- Melting point
- 212 · 212-214 °C(Solv: ethanol (64-17-5))
- Boiling point
- 645.9 · 645.9±55.0 °C(Predicted)
- Density
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- pka
- 13.38 · 13.38±0.70(Predicted)
- form
- Solid
Chemistry & industry
Applications
Uses6-Benzoylheteratisine is an Aconitum alkaloid with potential neuroprotective activity. 6-Benzoylheteratisine can antagonize tetrodotoxin, inhibit the increase of [Na+]i, [Ca2+]i and glutamate release, and block sodium channels. 6-Benzoylheteratisine has an inhibitory effect on the neuronal activity underlying epileptiform burst discharge[1][2].
Related reactions
0 records
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Compound notes
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