(S)-canadine
AlkaPlorer ID: AK001323
Synonym: 'Canadine, (.+-.)-', 'Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-, (.+-.)-', '(S)-canadine', 'SMR000393885', '(S)-Canadine', '(S)-(-)-Canadine', '6H-Benzog-1,3-benzodioxolo5,6-aquinolizine, 5,8,13,13a-tetrahydro-9,10,dimethoxy-, (.+-.)-', 'DL-Canadine', 'canadine l-form', 'Canadine', '(S)-Tetrahydroberberine', 'Tetrahydroumbellatine', 'MLS001202314', '(.+-.)-Canadine', 'Tetrahydroberberine', '(.+-.)-Tetrahydroberberine', 'CANADINE (DL-)', 'MLSMR', '(13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzog-1,3-benzodioxolo5,6-aquinolizine', 'Xanthopuccine'
IUPAC Name: (1R)-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
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-/m1/s1
InChIKey: VZTUIEROBZXUFA-MRXNPFEDSA-N
Reference
Formation of alkaloids in Corydalis ophiocarpa callus culture
PubChem CID: 443422
CAS: 2086-96-6
LOTUS: LTS0054524
SuperNatural Ⅲ: SN0404492-02
NPASS: NPC138487
Source
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 |
|---|---|---|---|---|---|
| Homo sapiens | Ataxin-2 | Potency | 22387.2 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | 1584.89 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | AC50 | 1258.93 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 1258.9 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2D6 | AC50 | 63.1 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | Potency | 63.1 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | AC50 | 7943.28 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 7943.3 | nM | None |
| Homo sapiens | Dopamine D1 receptor | Inhibition | 75.5 | % | 10.1016/j.bmc.2012.12.016 |
| Homo sapiens | Dopamine D1 receptor | Ki | 5000.0 | nM | 10.1016/j.bmc.2012.12.016 |
| Homo sapiens | Dopamine D2 receptor | Inhibition | 26.6 | % | 10.1016/j.bmc.2012.12.016 |
| Homo sapiens | Dopamine D2 receptor | Ki | nan | None | 10.1016/j.bmc.2012.12.016 |
| Homo sapiens | Geminin | Potency | 1835.6 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4A | Potency | 50118.7 | nM | None |
| Homo sapiens | Mothers against decapentaplegic homolog 3 | Potency | 4466.8 | nM | None |
| Homo sapiens | Prelamin-A/C | Potency | 354.8 | nM | None |
| Homo sapiens | Serotonin 1a (5-HT1a) receptor | Inhibition | 34.5 | % | 10.1016/j.bmc.2012.12.016 |
| Homo sapiens | Serotonin 1a (5-HT1a) receptor | Ki | nan | None | 10.1016/j.bmc.2012.12.016 |
| Homo sapiens | Serotonin 2a (5-HT2a) receptor | Inhibition | 18.3 | % | 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 | Tyrosyl-DNA phosphodiesterase 1 | Potency | 12995.3 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 14581.0 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 1412.5 | nM | None |
| Human immunodeficiency virus 1 | Aberrant vpr protein | Potency | 25118.9 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 369.6 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 720.8 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 2869.5 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 3696.4 | nM | None |
| None | Unchecked | Potency | 580.5 | nM | None |
| None | Unchecked | Potency | 10000.0 | nM | None |
| None | Unchecked | Potency | 11220.2 | nM | None |
| None | Unchecked | Potency | 39810.7 | nM | None |