1H-Indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine-12-carboxylic acid, 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-9-methoxy-, methyl ester, (12S,13aS,13bS)-
Basic information
- CAS
4752-37-8- Standard SMILES
CC[C@]12CCCN3CCc4c(n(c5cc(OC)ccc45)[C@@](O)(C(=O)OC)C1)[C@@H]32- InChIKey
QMSXPSURJTUZMP-HJNYFJLDSA-N- Molecular formula
- C22H28N2O4
- Average molar mass
- 384.5 g/mol
- Monoisotopic mass
- 384.20490738
Overview
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-4-methoxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraene-17-carboxylate has been reported in Vinca minor with data available.
Names & identifiers
- Preferred name
- 1H-Indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine-12-carboxylic acid, 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-9-methoxy-, methyl ester, (12S,13aS,13bS)-
- IUPAC
- methyl (15S,17S,19S)-15-ethyl-17-hydroxy-4-methoxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraene-17-carboxylate
- English name
- Vincine
- Molecular formula
- C22H28N2O4
- Molecular weight
- 384.46872
Names & synonyms
4752-37-8DTXSID9010991861H-Indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine-12-carboxylic acid, 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-9-methoxy-, methyl ester, (12S,13aS,13bS)-1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylic acid, 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-9-methoxy-, methyl ester, (12S,13aS,13bS)-RefChem:1058227DTXCID801530923VincineVinpocetine Impurity 33SCHEMBL30339367NS00094553Vincamine Impurity 26(3α,16α)-14,15-Dihydro-14β-hydroxy-11-methoxyeburnamenine-14α-carboxylic acid methyl ester
Database identifiers
- CAS
4752-37-8- PubChem CID
- 12444841
- DTXSID
DTXSID901099186- Nikkaji
- J143.554J
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 63.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 644
Physicochemical properties
- Melting point
- 212 · 212-4°C
- Boiling point
- 538.4 · 538.4±50.0 °C(Predicted)
- Density
- 1.36 · 1.36±0.1 g/cm3(Predicted)
- pka
- 12 · 12.00±0.40(Predicted)
Chemistry & industry
Applications
DescriptionOne of a number of alkaloids isolated from Vinca erecta RgL et Schmalh, this base crystallizes as colourless needles from MeOH. It has a specific rotation of [α]D + 36° (pyridine).
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