Limacusine
AlkaPlorer ID: AK035583
Synonym: '(-)-Cycleapeltine', 'Cycleapeltine', 'Homoaromoline', '(+)-Limacusine', 'Faralaotrine', 'Homothalicrine', 'Cycleapeltin', '(+)-Homoaromoline', '(+)-Thalrugosamine'
IUPAC Name: (1S,14S)-6,20,25-trimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),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(O)=C3OC3=C(OC)C=C4CCN(C)[C@@H](C2)C4=C3)CCN1C
InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)17-23-8-11-30(41-3)32(18-23)44-26-9-6-22(7-10-26)16-29-35-25(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-/m0/s1
InChIKey: YJRWQNIRFXVBRB-VMPREFPWSA-N
Reference
Cytotoxic and Antimalarial Bisbenzylisoquinoline Alkaloids from Cyclea barbata
PubChem CID: 3084718
CAS: 38849-80-8
LOTUS: LTS0217334
SuperNatural Ⅲ: SN0452263-03
NPASS: NPC42663
Source
Properties Information
Molecule Weight: 608.7350000000001
TPSA？: 72.86
MolLogP？: 6.859400000000008
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 | 3620.0 | nM | 10.1021/np980144f |
| Mus musculus | P388 | ED50 | 0.57 | ug ml-1 | 10.1021/np50091a004 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 29.0 | ng/ml | 10.1021/np50091a004 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 40.6 | ng/ml | 10.1021/np50091a004 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 48.0 | nM | 10.1021/np980144f |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 67.0 | nM | 10.1021/np980144f |
| None | NON-PROTEIN TARGET | ED50 | 2.2 | ug ml-1 | 10.1021/np50091a004 |
| None | NON-PROTEIN TARGET | ED50 | 4.4 | ug ml-1 | 10.1021/np50091a004 |
| None | Unchecked | Selectivity Index | 54.0 | None | 10.1021/np980144f |
| None | Unchecked | Selectivity Index | 76.0 | None | 10.1021/np980144f |