1.02010-04-08 22:09:40 UTC2019-11-26 03:04:58 UTCFDB011477(-)-alpha-NarcotineAlkaloid from Papaver somniferum (opium poppy)
Noscapine (also known as Narcotine, Nectodon, Nospen, and Anarcotine) is a benzylisoquinoline alkaloid from plants of the Papaveraceae family, without significant painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. It has also been shown to have anticancer activity. (-)-alpha-Narcotine is found in opium poppy.(-)-a-Narcotine(-)-Narcotine(-)-α-narcotineα-Narcotinea-Narcotinealpha-NarcotineCapvalCoscopinL-α-NarcotineL-alpha-NarcotineLongatinLyobexMethoxyhydrastineNarcomprenNarcosineNarcotinNarcotussinNarkotinNectadonNicolaneNipaxonNoscapalNoscapalinNoscapinNoscapinaNoscapineNoscapine (JP15/USP/INN)NoscapinumNoscopineo-MethylnarcotolineOpianOpianinOpianineTerbenolTusscapineVadebexα-narcotineC22H23NO7413.4205413.147452095(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-onenoscapine128-62-1[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1AKNNEGZIBPJZJG-MSOLQXFVSA-N belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.Phthalide isoquinolinesOrganic compoundsAlkaloids and derivativesPhthalide isoquinolinesAromatic heteropolycyclic compoundsAcetalsAlkyl aryl ethersAmino acids and derivativesAnisolesAralkylaminesAzacyclic compoundsBenzodioxolesBenzofuranonesCarboxylic acid estersHydrocarbon derivativesLactonesMonocarboxylic acids and derivativesOrganic oxidesOrganopnictogen compoundsOxacyclic compoundsPhthalidesTetrahydroisoquinolinesTrialkylaminesAcetalAlkyl aryl etherAmineAmino acid or derivativesAnisoleAralkylamineAromatic heteropolycyclic compoundAzacycleBenzenoidBenzodioxoleBenzofuranoneCarboxylic acid derivativeCarboxylic acid esterEtherHydrocarbon derivativeIsobenzofuranoneIsocoumaranLactoneMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacyclePhthalidePhthalide isoquinolineTertiary aliphatic amineTertiary amineTetrahydroisoquinolineIsoquinoline alkaloidsbenzylisoquinoline alkaloidcyclic acetalisobenzofuranonetertiary amino compoundlogp2.00logs-3.36solubility1.81e-01 g/lmelting_pointMp 176°logp2.58pka_strongest_acidic14.59pka_strongest_basic6.44iupac(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-oneaverage_mass413.4205mono_mass413.147452095smiles[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12formulaC22H23NO7inchiInChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1inchikeyAKNNEGZIBPJZJG-MSOLQXFVSA-Npolar_surface_area75.69refractivity107.08polarizability42.19rotatable_bond_count4acceptor_count7donor_count0physiological_charge0formal_charge0Specdb::CMs26289Specdb::CMs148285Specdb::MsMs72216Specdb::MsMs72217Specdb::MsMs72218Specdb::MsMs131061Specdb::MsMs131062Specdb::MsMs131063Specdb::MsMs374133Specdb::MsMs449581Specdb::MsMs449582Specdb::MsMs449809Specdb::MsMs449810Specdb::MsMs449811Specdb::MsMs451267Specdb::MsMs2242456Specdb::MsMs2244571Specdb::MsMs2247639Specdb::MsMs2248752Specdb::MsMs2249646Specdb::MsMs2250792Specdb::MsMs2251596Specdb::MsMs2678854Specdb::MsMs2678855Specdb::MsMs2678856Specdb::MsMs3030272Specdb::MsMs3030273HMDB33439#<Reference:0x0000555675f75820>Opium poppyType 1specificPapaver somniferum3469bitter