Compound: Lupinine
SMILES: OC[C@H]1[C@@H]2N(CCC1)CCCC2
InChIKey: HDVAWXXJVMJBAR-VHSXEESVSA-N
Synonyms: Lupinine, (-)-Lupinine, 486-70-4, [(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol, Octahydroquinolizine-1-methanol, 33BAJ73U1F, NSC-21723, CHEBI:28012, DTXSID00197565, 1S-cis-octahydro-2H-quinolizine-1-methanol, ((1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl)methanol, RefChem:924995, DTXCID60120056, 207-638-0, ((1R,9aR)-Octahydro-1H-quinolizin-1-yl)methanol, (+/-)-Lupinine, 10248-30-3, NSC 21723, Lupinine DL-form [MI], Lupinine, (+/-)-, (1R-trans)-Octahydro-2H-quinolizine-1-methanol, F74RAC8A5Q, (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol, (trans-Octahydro-1H-quinolizin-1-yl)methanol, [(1R,9aR)-octahydro-1H-quinolizin-1-yl]methanol, MFCD00213431, 2H-Quinolizine-1-methanol, octahydro-, (1R,9aR)-rel-, 2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-(+/-)-, (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE), ((1R,9aR)-octahydro-2H-quinolizin-1-yl)methanol, ((1R,2R)-6-azabicyclo[4.4.0]dec-2-yl)methan-1-ol, (R)-1-(Octahydro-quinolizin-1-yl)-methanol, l-lupinine, 2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-, (R,R)-1-(Hydroxymethyl)octahydroindolizine, [(1R,9aR)-Octahydro-2H-quinolizin-1-yl]methanol, EINECS 207-638-0, UNII-F74RAC8A5Q, BRN 0080447, UNII-33BAJ73U1F, (1R,9AR)-octahydro-2h-quinolizine-1-methanol, Spectrum_001736, SpecPlus_000606, LUPININE [MI], Spectrum2_000499, Spectrum3_001094, Spectrum4_001921, Spectrum5_000773, (-)-Lupinine, AldrichCPR, BSPBio_002768, KBioGR_002262, KBioSS_002216, 5-21-01-00338 (Beilstein Handbook Reference), DivK1c_006702, SCHEMBL177708, SPECTRUM1504021, SPBio_000397, CHEMBL459397, orb1311047, KBio1_001646, KBio2_002216, KBio2_004784, KBio2_007352, KBio3_001988, DTXSID80871679, HMS1922N13, Fr16605, NSC21723, CCG-38712, SBB000161, STK050782, AKOS004120072, EBC-616647, FL61612, SDCCGMLS-0066745.P001, BS-35956, DA-76298, ST018409, 2H-Quinolizine-1-methanol, (1R-trans)-, HY-121219, CS-0081248, NS00031813, F77309, (1R,9aR)-1-(Octahydroquinolizin-1-yl)methanol, F234394, Q412589, (1R,9aR)-1-(octahydro-quinolizin-1-yl)-methanol, BRD-K45978015-001-03-6
Theoretical properties:
molecular_formula: C10H19NO
molecular_weight: 169.26 g/mol
exact_mass: 169.146664230 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 12
topological_polar_surface_area: 23.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Lupinine is a quinolizidine alkaloid.
chembl: LUPININE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Lupinine is a quinolizidine alkaloid present in the genus Lupinus (colloquially referred to as lupins) of the flowering plant family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound as well as a vast number of studies on its biosynthesis from its natural precursor, lysine. Studies have shown that lupinine hydrochloride is a mildly toxic acetylcholinesterase inhibitor and that lupinine has an inhibitory effect on acetylcholine receptors. The characteristically bitter taste of lupin beans, which come from the seeds of Lupinus plants, is attributable to the quinolizidine alkaloids which they contain, rendering them unsuitable for human and animal consumption unless handled properly. However, because lupin beans have potential nutritional value due to their high protein content, efforts have been made to reduce their alkaloid content through the development of "sweet" varieties of Lupinus.