Compound: Matrine
SMILES: O=C1N2[C@@H]([C@@H]3[C@H]4N(CCC3)CCC[C@H]4C2)CCC1
InChIKey: ZSBXGIUJOOQZMP-JLNYLFASSA-N
Synonyms: Matrine, 519-02-8, (+)-Matrine, Vegard, N390W430AC, NSC-146051, DTXSID00274188, NSC-318810, (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one, (1R,2R,9S,17S)-7,13-diazatetracyclo(7.7.1.02,7.013,17)heptadecan-6-one, RefChem:55556, DTXCID70820575, 2,6-diamino-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-1H-pyrimidin-4-one, 7,13-diazatetracyclo(7.7.1.02,7.013,17)heptadecan-6-one, (7aS,13aR,13bR,13cS)-Dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, MFCD00210527, Matrene, (+)-, Alpha Matrine, CHEBI:6700, .alpha.-Matrine, (41S,7aS,13aR,13bR)-Dodecahydro-1H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10(41H)-one, alpha-Matrine, NSC 146051, BRN 0085851, Lupanidine, UNII-N390W430AC, Matrine CRS, Ex Sophporae Radix, Matrine (Standard), Matridin-15-one;, MATRINE [MI], Matrine ((+)-Matrine), MATRINE [WHO-DD], 5-24-02-00301 (Beilstein Handbook Reference), SCHEMBL177907, CHEMBL204860, HY-N0164R, HMS3884F13, HMS6019G05, HY-N0164, BDBM50249581, Matridin-15-one; Vegard; -Matrine, MSK000575, NSC146051, s2322, Matridin-15-one;Vegard;alpha-Matrine, AKOS007930266, CCG-208589, CS-1601, EBC-466111, FM65961, KS-5203, Matrine 100 microg/mL in Acetonitrile, NCGC00346593-01, SY016076, M2120, NS00066991, AA-504/21004001, AL-466/21199007, AO-228/21245001, (1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecan-6-one, (4(1)S,7aS,13aR,13bR)-dodecahydro-1H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10(4(1)H)-one, (7aS,13aR,13bS,13cS)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3,2,1-ij][1,6]naphthyridin-10-one, 1H,5H,10H-DIPYRIDO(2,1-F:3',2',1'-IJ)(1,6)NAPHTHYRIDIN-10-ONE, DODECAHYDRO-, (7AS,13AR,13BR,13CS)-
Theoretical properties:
molecular_formula: C15H24N2O
molecular_weight: 248.36 g/mol
exact_mass: 248.188863393 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 18
topological_polar_surface_area: 23.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Matrine is an alkaloid.
chembl: MATRINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Matrine is an alkaloid found in plants from the family Fabaceae. It has a variety of pharmacological effects, including in-vitro anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism.
Matrine possesses strong antitumor activities in vitro and in vivo. Inhibition of cell proliferation and induction of apoptosis are the likely mechanisms responsible for matrine's antitumor activities. Matrine can be commercially extracted from the traditional Chinese medical herb Sophora flavescens Ait.
Mu opioid agonism is associated with euphoria, while kappa opioid agonism is associated with dysphoria and psychotomimetic hallucinations (as seen in the kappa-agonist Salvinorin A). Both receptors are known to produce analgesia when activated.
Matrine and the related compound oxymatrine have a toxic effect against the formosan subterranean termite. Additionally, it acts as a nematicide against the pine wood nematode which causes pine wilt, as well as pathogenic nematodes which target humans.
Matrine alleviates neuro-inflammation and oxidative stress in the brain caused by acute liver injury, thus producing antianxiety and antidepression effects.