1.0 2011-09-21 00:26:55 UTC 2025-11-19 02:43:35 UTC FDB023249 Protopine Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic [HMDB] 4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one 7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one Biflorine Corydinine Fumarine Hypercorine Macleyine Protopin C20H19NO5 353.3686 353.126322723 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0⁴,¹².0⁶,¹⁰.0¹⁸,²²]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one protopine 130-86-9 CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2 InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3 GPTFURBXHJWNHR-UHFFFAOYSA-N belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Protopine alkaloids Organic compounds Alkaloids and derivatives Protopine alkaloids Aromatic heteropolycyclic compounds Acetals Aralkylamines Aryl alkyl ketones Azacyclic compounds Benzenoids Benzodioxoles Hydrocarbon derivatives Organic oxides Organopnictogen compounds Oxacyclic compounds Trialkylamines Acetal Amine Aralkylamine Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Azacycle Benzenoid Benzodioxole Hydrocarbon derivative Ketone Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Protopine skeleton Tertiary aliphatic amine Tertiary amine Isoquinoline alkaloids a small molecule dibenzazecine alkaloid Solid logp 1.95 ALOGPS logs -3.24 ALOGPS solubility 2.02e-01 g/l ALOGPS logp 2.59 ChemAxon pka_strongest_acidic 15.82 ChemAxon pka_strongest_basic 4.95 ChemAxon iupac 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0⁴,¹².0⁶,¹⁰.0¹⁸,²²]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one ChemAxon average_mass 353.3686 ChemAxon mono_mass 353.126322723 ChemAxon smiles CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC2=C(C1)C1=C(OCO1)C=C2 ChemAxon formula C20H19NO5 ChemAxon inchi InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3 ChemAxon inchikey GPTFURBXHJWNHR-UHFFFAOYSA-N ChemAxon polar_surface_area 57.23 ChemAxon refractivity 94.57 ChemAxon polarizability 36.68 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 26 Specdb::CMs 2139 Specdb::CMs 22839 Specdb::CMs 31490 Specdb::CMs 130964 Specdb::CMs 138698 Specdb::MsMs 83202 Specdb::MsMs 83203 Specdb::MsMs 83204 Specdb::MsMs 144750 Specdb::MsMs 144751 Specdb::MsMs 144752 Specdb::MsMs 445351 Specdb::MsMs 445352 Specdb::MsMs 446817 Specdb::MsMs 446818 Specdb::MsMs 446819 Specdb::MsMs 446820 Specdb::MsMs 446821 Specdb::MsMs 447273 Specdb::MsMs 449437 Specdb::MsMs 449440 Specdb::MsMs 449443 Specdb::MsMs 452167 Specdb::MsMs 2226834 Specdb::MsMs 2227869 Specdb::MsMs 2231636 Specdb::MsMs 2232629 Specdb::MsMs 2236254 Specdb::MsMs 2238386 Specdb::MsMs 2239175 HMDB03920 16415 #<Reference:0x000055ce335cab50> #<Reference:0x000055ce335ca970> #<Reference:0x000055ce335ca768> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823