Mamanine
Basic information
- CAS
60394-92-5- Standard SMILES
O=c1cccc([C@@H]2C[C@H](CO)[C@H]3CCCCN3C2)[nH]1- InChIKey
JAUFYQKXSPWZRV-YRGRVCCFSA-N- Molecular formula
- C15H22N2O2
- Average molar mass
- 262.35 g/mol
- Monoisotopic mass
- 262.16812795
Overview
Mamanine has been reported in Sophora chrysophylla and Sophora flavescens with data available.
Names & identifiers
- Preferred name
- Mamanine
- IUPAC
- 6-[(1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl]-1H-pyridin-2-one
- English name
- mamanine
- Molecular formula
- C15H22N2O2
- Molecular weight
- 262.35
Names & synonyms
MAMANINE60394-92-5DTXSID902091466-[(1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl]-1H-pyridin-2-one6-((1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl)-1H-pyridin-2-oneRefChem:155534DTXCID101316372(1H)-Pyridinone, 6-(octahydro-1-(hydroxymethyl)-2H-quinolizin-3-yl)-, (1alpha,3alpha,9aalpha)-(+)-SCHEMBL563305orb1696189AKOS040752921T33170
Show more names
6-[(1S,9aβ)-Octahydro-1β-(hydroxymethyl)-2H-quinolizine-3β-yl]pyridine-2(1H)-one2(1H)-Pyridinone, 6-[(1R,3S,9aS)-octahydro-1-(hydroxymethyl)-2H-quinolizin-3-yl]-, rel-(+)-
6-[(1S,3R,9aR)-1-(Hydroxymethyl)octahydro-2H-quinolizin-3-yl]pyridin-2(1H)-one
Database identifiers
- CAS
60394-92-5- PubChem CID
- 3085182
- DTXSID
DTXSID90209146- Nikkaji
- J238.701H
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 416
Physicochemical properties
- Melting point
- 17 l-2°C · 17l-2°C
- Boiling point
- 483.273 · 483.273±45.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.211 · 1.211±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 11.565 · 11.565±0.10(predicted)
Chemistry & industry
Applications
DescriptionThis novel alkaloid occurs in the bark of Sophora chrysophylla and is obtained in the form of colourless crystals of the dihydrate which have the above melting point after prior melting at 100-4°C followed by resolidification. The base has been characterized as the crystalline cyclohexylsulphonate, m.p. 245-252°C and the diacetate which forms colourless needles that decompose on standing at room temperature. The free base is optically active with a specific rotation of [α]24.3/sup>D + 31.7° (c 2.32, EtOH). Mamaine is an intermediate in a previously unknown biogenetic pathway of the Sophora alkaloids (cf. Pohakuline).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…