Canadine; (±)-form
AlkaPlorer ID: AK062236
Synonym: None
IUPAC Name: 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=C2CC3C4=CC5=C(C=C4CCN3CC2=C1OC)OCO5
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
InChIKey: VZTUIEROBZXUFA-UHFFFAOYSA-N
Reference
PubChem CID: 34458
CAS: 5096-57-1
LOTUS: LTS0116620
NPASS: NPC41178
COCONUT: CNP0410168.2
data_source: manually
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Corydalis | Papaveraceae | Ranunculales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
| None | Corydalis | 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 |
|---|---|---|---|---|---|
| Acinetobacter baumannii | Acinetobacter baumannii | Inhibition | -8.62 | % | 10.6019/CHEMBL4296183 |
| Bacteria | DNA | EC50 | 93000.0 | nM | 10.1016/j.bmc.2018.08.038 |
| Candida albicans | Candida albicans | Inhibition | -1.05 | % | 10.6019/CHEMBL4296183 |
| Cryptococcus neoformans | Cryptococcus neoformans | Inhibition | -13.18 | % | 10.6019/CHEMBL4296183 |
| Escherichia coli | Escherichia coli | Inhibition | 7.87 | % | 10.6019/CHEMBL4296183 |
| Homo sapiens | 786-0 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A498 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A549 | IC50 | 30000.0 | nM | 10.1016/j.bmcl.2010.06.035 |
| Homo sapiens | ACHN | GI50 | 100000.0 | nM | None |
| Homo sapiens | Amyloid-beta A4 protein | Inhibition | -28.0 | % | 10.1016/j.ejmech.2021.113289 |
| Homo sapiens | Bromodomain adjacent to zinc finger domain protein 2B | Potency | 89125.1 | nM | None |
| Homo sapiens | BT-549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 10000.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 100000.0 | nM | None |
| Homo sapiens | Coagulation factor III | IC50 | 8.35 | nM | 10.1016/j.bmc.2012.11.002 |
| Homo sapiens | COLO 205 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Cyclin-dependent kinase 2 | IC50 | 50000.0 | nM | 10.1016/j.bmcl.2010.01.007 |
| Homo sapiens | DU-145 | GI50 | 100000.0 | nM | None |
| Homo sapiens | EKVX | GI50 | 100000.0 | nM | None |
| Homo sapiens | Guanine nucleotide-binding protein G(s), subunit alpha | Potency | 3981.1 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-15 | IC50 | 30000.0 | nM | 10.1016/j.bmcl.2010.06.035 |
| Homo sapiens | HEK293 | Potency | 562.3 | nM | None |
| Homo sapiens | HL-60 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 100000.0 | nM | None |
| Homo sapiens | HT-29 | GI50 | 30831.88 | nM | None |
| Homo sapiens | HT-29 | GI50 | 76032.63 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | K562 | GI50 | 79983.43 | nM | None |
| Homo sapiens | K562 | GI50 | 100000.0 | nM | None |
| Homo sapiens | KM12 | GI50 | 100000.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 100000.0 | nM | None |
| Homo sapiens | M14 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 100000.0 | nM | None |
| Homo sapiens | MCF7 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-N | GI50 | 100000.0 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 14125.4 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 68706.84 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 60953.69 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCTC-2544 | Activity | nan | None | 10.1016/j.bmc.2018.08.038 |
| Homo sapiens | OVCAR-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Parathyroid hormone receptor | Potency | 125892.5 | nM | None |
| Homo sapiens | PC-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-268 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-539 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-2 | IC50 | 27940.0 | nM | 10.1016/j.bmcl.2010.06.035 |
| Homo sapiens | SK-MEL-28 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-OV-3 | IC50 | 30000.0 | nM | 10.1016/j.bmcl.2010.06.035 |
| Homo sapiens | SN12C | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SR | GI50 | 100000.0 | nM | None |
| Homo sapiens | SW-620 | GI50 | 100000.0 | nM | None |
| Homo sapiens | T47D | GI50 | 100000.0 | nM | None |
| Homo sapiens | TK-10 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 11374.3 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 12762.2 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 20596.2 | nM | None |
| Homo sapiens | U-251 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UO-31 | GI50 | 100000.0 | nM | None |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 reverse transcriptase | IC50 | 200.0 | ug.mL-1 | 10.1021/np50073a012 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 reverse transcriptase | Inhibition | 25.0 | % | 10.1016/j.ejmech.2011.01.016 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 reverse transcriptase | Inhibition | 25.0 | % | 10.1021/np50073a012 |
| Klebsiella pneumoniae | Klebsiella pneumoniae | Inhibition | -2.26 | % | 10.6019/CHEMBL4296183 |
| Mus musculus | BV-2 | Activity | 45.0 | % | 10.1016/j.bmc.2018.10.020 |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 1471.6 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 9285.0 | nM | None |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | Inhibition | 8.62 | % | 10.6019/CHEMBL4296183 |
| Rattus norvegicus | Alpha-1a adrenergic receptor | Ki | 1122.02 | nM | 10.1021/acs.jmedchem.6b01217 |
| Rattus norvegicus | PC-12 | CC50 | 150000.0 | nM | 10.1016/j.ejmech.2021.113289 |
| Schistosoma mansoni | Thioredoxin glutathione reductase | Potency | 35481.3 | nM | None |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 19952.62 | nM | 10.6019/CHEMBL4651402 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 20000.0 | nM | 10.6019/CHEMBL4651402 |
| Staphylococcus aureus | Staphylococcus aureus | Inhibition | 10.57 | % | 10.6019/CHEMBL4296183 |
| None | No relevant target | Activity | 1577.0 | equiv | 10.1016/j.bmc.2018.08.038 |
| None | No relevant target | Solubility | 7000.0 | nM | 10.1016/j.ejmech.2021.113289 |
| None | Unchecked | Ac50 | 31.62 | uM | None |
| None | Unchecked | Ac50 | 39.81 | uM | None |
| None | Unchecked | Ac50 | 44.67 | uM | None |
| None | Unchecked | AC50 | 31622.8 | nM | None |
| None | Unchecked | AC50 | 39810.7 | nM | None |
| None | Unchecked | AC50 | 44668.4 | nM | None |
| None | Unchecked | EC50 | 3430.0 | nM | None |
| None | Unchecked | EC50 | 60000.0 | nM | None |
| None | Unchecked | Potency | 8912.5 | nM | None |
| None | Unchecked | Potency | 31622.8 | nM | None |