Vomicine
Basic information
- CAS
125-15-5- Standard SMILES
CN1CC[C@]23C(=O)C[C@H]4C(=CCO[C@H]5CC(=O)N(c6c(O)cccc62)[C@H]3[C@H]54)C1- InChIKey
ZMTYENXGROJCEA-LNKPQSDASA-N- Molecular formula
- C22H24N2O4
- Average molar mass
- 380.4 g/mol
- Monoisotopic mass
- 380.17360725
Overview
Vomicine is a member of carbazoles.
Names & identifiers
- Preferred name
- Vomicine
- IUPAC
- (1S,10S,22R,23R,24S)-15-hydroxy-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14(19),15,17-tetraene-12,20-dione
- English name
- vomicine
- Molecular formula
- C22H24N2O4
- Molecular weight
- 380.44
Names & synonyms
Vomicine125-15-5StrychnicineVomicin4R9445MB8M(1S,10S,22R,23R,24S)-15-hydroxy-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14(19),15,17-tetraene-12,20-dione12H-6a,4-(Ethaniminomethano)indolo[3,2,1-ij]oxepino[2,3,4-de]quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hexahydro-10-hydroxy-16-methyl-, (4aR,6aS,13aS,13bR,13cS)-4-Hydroxy-19-methyl-16,19-secostrychnidine-10,16-dioneUNII-4R9445MB8M12H-6A,4-(ETHANIMINOMETHANO)INDOLO(3,2,1-IJ)OXEPINO(2,3,4-DE)QUINOLINE-6,12(2H)-DIONE, 4A,5,13,13A,13B,13C-HEXAHYDRO-10-HYDROXY-16-METHYL-, (4AR,6AS,13AS,13BR,13CS)-Vomicine (Standard)VOMICINE [MI]
Show more names
C09255StruxineVomicine, 10 mM in DMSO12-Hydroxy-N-methylpseudostrychinine4-Hydroxy-19-methyl-16,19-secostrychinidine-10,16-dioneinhibit,Inhibitor,activity,Vomicine,alkaloid,antidiabetic
16,19-Secostrychnidine-10,16-dione, 4-hydroxy-19-methyl-orb1218991orb1297603SCHEMBL3371643CHEMBL2164625CHEBI:10019HY-N2616RDTXSID30154540
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 70.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 766
Physicochemical properties
- Melting point
- 286 · 286-290℃ (dec.)
- alpha
- 22 · D22 +80° (c = 0.5 in alc)
- Boiling point
- 508.07 °C · 508.07°C (rough estimate)
- Density
- 1.44 · 1.44±0.1 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.65 · 1.6500 (estimate)
- pka
- 9.18 · 9.18±0.20(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- ZMTYENXGROJCEA-LNKPQSDASA-N
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 R9445MB8M · 4R9445MB8M
Chemistry & industry
Applications
DescriptionSchaefer has obtained this base from old seeds of Strychnos Nux-vomica which had deteriorated where is occurs to the extent of about 0.1 per cent. It forms colourless crystals from EtOH which become yellow on exposure to light. With H2S04 it gives a colourless solution that becomes green on the addition of potassium dichromate. From the available evidence it seems likely that it is not a true alkaloid but a decomposition product of either strychnine or brucine.
UsesVomicine is an antiplasmoidal alkaloid extracted from the stem bark of Strychnos malacoclados and is useful against malaria.
Additional notes
DefinitionChEBI: Vomicine is a member of carbazoles.
Related reactions
0 records
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Compound notes
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