Compound: Sinomenine
SMILES: O=C1C(OC)=C[C@@H]2[C@H]3N(C)CC[C@]2(C1)c4c(O)c(OC)ccc4C3
InChIKey: INYYVPJSBIVGPH-QHRIQVFBSA-N
Synonyms: Sinomenine, 115-53-7, Kukoline, Cucoline, Coculine, Sabianine A, 63LT81K70N, morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-, (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one, cuculine, (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo(7.5.3.01,10.02,7)heptadeca-2(7),3,5,11-tetraen-13-one, RefChem:183169, 4-hydroxy-3,7-dimethoxy-17-methylmorphin-7-en-6-one, 204-094-6, CCRIS 1550, SINOMENIN, (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one, CHEMBL248095, (1R,9S,10R)-3-Hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one, (4bR,8aS,9S)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one, morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9alpha,13alpha,14alpha)-, hydrochloride, NSC76021, SR-05000002170, EINECS 204-094-6, BRN 0095280, UNII-63LT81K70N, Sinomenine CRS, Orientvine stem HRS, Sinomenine (Cucoline), SINOMENINE [MI], Spectrum2_001242, Spectrum3_001134, Spectrum4_001981, Spectrum5_001621, UPCMLD-DP085, 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one, SINOMENINE [WHO-DD], BSPBio_002627, KBioGR_002508, 5-21-13-00516 (Beilstein Handbook Reference), SCHEMBL363812, SPECTRUM1505253, SPBio_001144, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one, CHEBI:9163, NP51, orb1305106, orb3140484, SCHEMBL29474810, UPCMLD-DP085:001, BCBcMAP01_000195, KBio3_002127, DTXSID00871595, BDBM224031, ALBB-020908, MSK10242, BDBM50241298, CCG-39100, EBC-11066, NSC785175, s2359, AKOS000265568, AKOS015960539, AKOS016023715, AC-8025, FS09811, NSC-785175, 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9|A,13|A,14|A)-, SMP1_000273, NCGC00161641-01, NCGC00161641-02, NCGC00161641-04, NCGC00161641-05, BS-42101, HY-15122, Sinomenine 100 microg/mL in Acetonitrile, CS-0003778, NS00018030, SW219295-1, C09643, Sinomenine, 0.3 mol chloroform of crystallization, Q7524904, SR-05000002170-2, SR-05000002170-3, BRD-K83459933-001-02-1, BRD-K83459933-001-05-4, (9|_,13|_,14|_)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one, 4-Hydroxy-3,7-dimethoxy-17-methyl-9alpha,13alpha,14alpha-7,8-didehydromorphinan-6-one, Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9a,13a,14a)-, (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0(1),(1)?.0(2),?]heptadeca-2(7),3,5,11-tetraen-13-one, (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one, MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4-HYDROXY-3,7-DIMETHOXY-17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-
Theoretical properties:
molecular_formula: C19H23NO4
molecular_weight: 329.4 g/mol
exact_mass: 329.16270821 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 24
topological_polar_surface_area: 59 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Sinomenine is a morphinane alkaloid.
chembl: SINOMENINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Sinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum which is native to Japan and China. The plant is traditionally used in herbal medicine in these countries for rheumatism and arthritis. However, analgesic action against other types of pain seems to be limited. Sinomenine is a morphinan derivative that is related to the common cough suppressant dextromethorphan. The drug's anti-rheumatic effects are thought to be primarily mediated via release of histamine, but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved.