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Canadine

AlkaPlorer ID: AK001324

Synonym: None

IUPAC Name: (1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene

Structure

SMILES: COC1=CC=C2C[C@H]3C4=CC5=C(C=C4CCN3CC2=C1OC)OCO5

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InChI: InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3/t16-/m0/s1

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InChIKey: VZTUIEROBZXUFA-INIZCTEOSA-N

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Reference

Alkaloids of<i>Corydalis cheilanthifolia</i>

PubChem CID: 21171

CAS: 5096-57-1

LOTUS: LTS0147391

SuperNatural Ⅲ: SN0404492-01

NPASS: NPC216459

data_source: manually

Source

Species Genus Family Order Class Phylum Kingdom Domain
Fibraurea recisa Fibraurea Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ulex airensis Ulex Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stachys plumosa Stachys Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hydrastis canadensis Hydrastis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phellodendron chinense Phellodendron Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper methysticum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis yanhusuo Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artabotrys maingayi Artabotrys Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dovyalis hebecarpa Dovyalis Salicaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ixeris repens Ixeris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Diospyros ebenum Diospyros Ebenaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Eremophila oppositifolia Eremophila Scrophulariaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Taxillus yadoriki Taxillus Loranthaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ligularia sagitta Ligularia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Angelica dahurica Angelica Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lappula echinata Lappula Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis ophiocarpa Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thuja plicata Thuja Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Corydalis ternata Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stereocaulon alpinum Stereocaulon Stereocaulaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Tylopilus plumbeoviolaceus Tylopilus Boletaceae Boletales Agaricomycetes Basidiomycota Fungi Eukaryota
Labidiaster annulatus Labidiaster Labidiasteridae Forcipulatida Asteroidea Echinodermata Metazoa Eukaryota
Senna spectabilis Senna Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Chaetomorpha moniligera Chaetomorpha Cladophoraceae Cladophorales Ulvophyceae Chlorophyta Viridiplantae Eukaryota
Lasius niger Lasius Formicidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota
Streptomyces aizunensis Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Symphytum officinale Symphytum Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dictyostelium longosporum Dictyostelium Dictyosteliaceae Dictyosteliales Eumycetozoa Evosea None Eukaryota
Corydalis turtschaninovii Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penicillium vulpinum Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Phellodendron amurense Phellodendron Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Psacalium peltatum Psacalium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Chelidonium majus Chelidonium Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 339.3910000000001

TPSA？: 40.16

MolLogP？: 3.088000000000001

Number of H-Donors: 0

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Candida albicans Candida albicans Activity nan None 10.1021/np9701889
Drosophila melanogaster Drosophila melanogaster LD50 2.5 ug 10.1021/jf201401j
Entamoeba histolytica Entamoeba histolytica IC50 42.71 ug.mL-1 10.1007/s00044-011-9767-1
Entamoeba histolytica Entamoeba histolytica IC50 126000.0 nM 10.1021/np000144r
Escherichia coli Escherichia coli Activity nan None 10.1016/j.bmcl.2005.11.045
Homo sapiens Alpha-1a adrenergic receptor IC50 5400.0 nM 10.1021/acs.jmedchem.6b01217
Homo sapiens Dopamine D1 receptor Inhibition 98.3 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D1 receptor Ki 48.6 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D1 receptor Ki 66.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Inhibition 88.7 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Ki 80.2 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D2 receptor Ki 119.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D3 receptor Ki 433.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D4 receptor Ki 486.0 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens Dopamine D5 receptor Ki 62.1 nM 10.1016/j.bmcl.2017.01.090
Homo sapiens HeLa Activity nan None 10.1016/j.bmc.2008.02.015
Homo sapiens HepG2 Activity nan None 10.1016/j.bmc.2008.02.015
Homo sapiens HepG2 FC 1.0 None 10.1021/jm801157z
Homo sapiens KB IC50 734000.0 nM 10.1021/np000144r
Homo sapiens MRC5 CC50 125000.0 nM 10.1016/j.bmcl.2006.12.085
Homo sapiens Serotonin 1a (5-HT1a) receptor Inhibition 84.4 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 5000.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 46.6 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki nan None 10.1016/j.bmc.2012.12.016
Homo sapiens Sulfonylurea receptor 1, Kir6.2 Activity nan None 10.1016/j.bmcl.2005.11.045
Human betaherpesvirus 5 Human betaherpesvirus 5 IC50 12000.0 nM 10.1016/j.bmcl.2006.12.085
Klebsiella pneumoniae Klebsiella pneumoniae Activity nan None 10.1021/np9701889
Mus musculus Mus musculus T-C 0.1 day 10.1021/jm00401a006
Mus musculus Mus musculus T-C 0.3 day 10.1021/jm00401a006
Mycobacterium intracellulare Mycobacterium intracellulare MIC 50.0 ug.mL-1 10.1021/np9701889
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 50.0 ug.mL-1 10.1021/np9701889
Mycolicibacterium smegmatis Mycolicibacterium smegmatis Activity nan None 10.1021/np9701889
Plasmodium falciparum Plasmodium falciparum IC50 0.555 ug.mL-1 10.1021/jm00401a006
Plasmodium falciparum Plasmodium falciparum IC50 1.739 ug.mL-1 10.1021/jm00401a006
Plasmodium falciparum Plasmodium falciparum IC50 1640.0 nM 10.1021/np000144r
Plasmodium falciparum Plasmodium falciparum IC50 5130.0 nM 10.1021/np000144r
Plasmodium falciparum Plasmodium falciparum IC50 147000.0 nM 10.1021/np000144r
Rattus norvegicus Aorta Activity 11.2 % 10.1021/np980471n
Rattus norvegicus Aorta Activity 13.6 % 10.1021/np980471n
Rattus norvegicus Aorta Activity 25.6 % 10.1021/np980471n
Rattus norvegicus Aorta Activity 49.8 % 10.1021/np980471n
Rattus norvegicus Aorta Activity 70.0 % 10.1021/np980471n
Rattus norvegicus Aorta Activity 79.1 % 10.1021/np980471n
Rattus norvegicus Aorta Activity 82.8 % 10.1021/np980471n
Rattus norvegicus Hepatocyte Activity 80.0 % 10.1016/j.bmc.2008.02.015
Rattus norvegicus Hepatocyte Activity 95.0 % 10.1016/j.bmc.2008.02.015
Rattus norvegicus Hepatocyte Activity nan None 10.1016/j.bmc.2008.02.015
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/np9701889
Toxoplasma gondii Toxoplasma gondii ID50 8.7 uM 10.1016/j.bmcl.2012.02.038
None ADMET TD50 210.0 uM 10.1016/j.bmcl.2012.02.038
None ADMET TI 24.0 None 10.1016/j.bmcl.2012.02.038
None NON-PROTEIN TARGET Activity 45.8 % 10.1021/np980471n
None NON-PROTEIN TARGET Activity 54.7 % 10.1021/np980471n
None NON-PROTEIN TARGET Activity 76.4 % 10.1021/np980471n
None NON-PROTEIN TARGET Activity 91.2 % 10.1021/np980471n
None Unchecked Ratio CC50/IC50 10.0 None 10.1016/j.bmcl.2006.12.085

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011666 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4 1.1.3.36-RXN
AKRT011895 COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4.C[SAH]>>COc1ccc2c(c1OC)C[N+]1(C)CCc3cc4c(cc3[C@@H]1C2)OCO4 RXN-13806
AKRT011896 COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4>>COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2 TETRAHYDROBERBERINE-OXIDASE-RXN
AKRT011930 COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4 None