protopine
AlkaPlorer ID: AK002947
Synonym: "4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one", 'Protopine hydrochloride', 'Fumarine', 'Protopine', 'Biflorine', 'Macleyine', '7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride', 'protopine', 'ARGEMONINE', "Bis1,3benzodioxolo4,5-c:5',6'-gazecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-, hydrochloride", 'Corydinine', "7-methyl-6,8,9,16-tetrahydrobis1,3benzodioxolo4,5-c:5',6'-gazecin-15(7H)-one", 'ARGEMONINE (PROTOPINE', 'Fumarin', 'PROTOPINE'
IUPAC Name: 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
Structure
SMILES: CN1CCC2=CC3=C(C=C2C(=O)CC2=C(C1)C1=C(C=C2)OCO1)OCO3
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
InChIKey: GPTFURBXHJWNHR-UHFFFAOYSA-N
Reference
Alkaloids from Egyptian Papaver rhoeas
PubChem CID: 4970
CAS: 130-86-9
LOTUS: LTS0080245
SuperNatural Ⅲ: SN0112102
NPASS: NPC308267
COCONUT: CNP0214801
data_source: manually
Source
Properties Information
Molecule Weight: 353.3740000000001
TPSA？: 57.23
MolLogP？: 2.557300000000001
Number of H-Donors: 0
Number of H-Acceptors: 6
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Giardia intestinalis | Putative fructose-1,6-bisphosphate aldolase | Potency | 7062.7 | nM | None |
| Homo sapiens | Acetylcholinesterase | IC50 | 100000.0 | nM | 10.1021/acs.jnatprod.7b00847 |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 10000.0 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | Potency | 50.1 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 25118.9 | nM | None |
| Homo sapiens | GES1 | IC50 | 150000.0 | nM | 10.1016/j.bmc.2022.116705 |
| Homo sapiens | HGC-27 | IC50 | 121300.0 | nM | 10.1016/j.bmc.2022.116705 |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 31622.8 | nM | None |
| Homo sapiens | MGC-803 | IC50 | 94500.0 | nM | 10.1016/j.bmc.2022.116705 |
| Homo sapiens | Thyroid stimulating hormone receptor | Potency | 12589.3 | nM | None |
| Leishmania donovani | Leishmania donovani | IC50 | 90.0 | ug.mL-1 | 10.1016/j.bmcl.2019.126642 |
| Rattus norvegicus | Inositol monophosphatase 1 | Potency | 11220.2 | nM | None |
| Trypanosoma brucei rhodesiense | Trypanosoma brucei rhodesiense | IC50 | 8.71 | ug.mL-1 | 10.1016/j.bmcl.2019.126642 |
| Trypanosoma cruzi | Trypanosoma cruzi | IC50 | 46.27 | ug.mL-1 | 10.1016/j.bmcl.2019.126642 |
| None | Unchecked | Potency | 17782.8 | nM | None |
| None | Unchecked | Potency | 35481.3 | nM | None |