fangchinoline
AlkaPlorer ID: AK005853
Synonym: 'dl-Fangchinoline', '', 'Limacine', 'Frangchinoline', "(1beta)-2,2'-dimethyl-6,6',12-trimethoxyberbaman-7-ol", 'Cycleadrine', '7-O-Demethyltetrandrine', '7-O-Demethyltetrandine', '(+)-fangchinoline', '(-)-Limacine', '(+)-limacine', 'Fangchinoline', '7-O-demethyltetrandrine'
IUPAC Name: (1R,14R)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-21-ol
Structure
SMILES: COC1=CC=C2C=C1OC1=CC=C(C=C1)C[C@@H]1C3=C(C=C(OC)C(=C3)OC3=C4C(=CC(OC)=C3O)CCN(C)[C@@H]4C2)CCN1C
InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m1/s1
InChIKey: IIQSJHUEZBTSAT-FQLXRVMXSA-N
Reference
Bisbenzylisoquinoline Alkaloids from Cyclea barbata
PubChem CID: 7656034
LOTUS: LTS0146090
SuperNatural Ⅲ: SN0146669-01
NPASS: NPC182052
Source
Properties Information
Molecule Weight: 608.7350000000001
TPSA？: 72.86
MolLogP？: 6.859400000000009
Number of H-Donors: 1
Number of H-Acceptors: 8
RingCount: 8
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | KB | ED50 | 16100.0 | nM | 10.1021/np980144f |
| Mus musculus | P388 | ED50 | 0.25 | ug ml-1 | 10.1021/np50091a004 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 52.7 | ng/ml | 10.1021/np50091a004 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 164.0 | ng/ml | 10.1021/np50091a004 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 86.0 | nM | 10.1021/np980144f |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 263.0 | nM | 10.1021/np980144f |
| None | NON-PROTEIN TARGET | ED50 | 9.8 | ug ml-1 | 10.1021/np50091a004 |
| None | NON-PROTEIN TARGET | ED50 | 11.0 | ug ml-1 | 10.1021/np50091a004 |
| None | Unchecked | Selectivity Index | 61.0 | None | 10.1021/np980144f |
| None | Unchecked | Selectivity Index | 186.0 | None | 10.1021/np980144f |