Gyrocarpine
AlkaPlorer ID: AK044325
Synonym: '(+)-Stephibaberine', '', 'Gyrocarpine', 'Stephibaberine'
IUPAC Name: (1R,14S)-6,21,25-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-20-ol
Structure
SMILES: COC1=CC=C2C=C1OC1=CC=C(C=C1)C[C@H]1C3=C(C=C(O)C(OC)=C3OC3=C(OC)C=C4CCN(C)[C@H](C2)C4=C3)CCN1C
InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-20-32(42-4)34-21-27(24)28(38)17-23-8-11-31(41-3)33(18-23)44-26-9-6-22(7-10-26)16-29-35-25(13-15-39(29)2)19-30(40)36(43-5)37(35)45-34/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m1/s1
InChIKey: VXPVPAHQYCJDTP-WDYNHAJCSA-N
Reference
Cytotoxic and Antimalarial Bisbenzylisoquinolme Alkaloids from Stephania erecta
PubChem CID: 9938773
LOTUS: LTS0001071
NPASS: NPC311973
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 | A-431 | ED50 | 8.9 | ug ml-1 | 10.1021/np50091a005 |
| Homo sapiens | HT-1080 | ED50 | 7.2 | ug ml-1 | 10.1021/np50091a005 |
| Homo sapiens | KB | ED50 | 6.4 | ug ml-1 | 10.1021/np50091a005 |
| Homo sapiens | KB | ED50 | 10500.0 | nM | 10.1021/np980144f |
| Homo sapiens | LNCaP | ED50 | 8.3 | ug ml-1 | 10.1021/np50091a005 |
| Homo sapiens | SK-MEL-2 | ED50 | 12.8 | ug ml-1 | 10.1021/np50091a005 |
| Homo sapiens | ZR-75-1 | ED50 | 1.2 | ug ml-1 | 10.1021/np50091a005 |
| Mus musculus | P388 | ED50 | 3.7 | ug ml-1 | 10.1021/np50091a005 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 130.0 | ng/ml | 10.1021/np50091a005 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 310.0 | ng/ml | 10.1021/np50091a005 |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 214.0 | nM | 10.1021/np980144f |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 510.0 | nM | 10.1021/np980144f |
| None | ADMET | ED50 | 4.7 | ug ml-1 | 10.1021/np50091a005 |
| None | ADMET | ED50 | 7.4 | ug ml-1 | 10.1021/np50091a005 |
| None | ADMET | ED50 | 7.5 | ug ml-1 | 10.1021/np50091a005 |
| None | ADMET | ED50 | 9.0 | ug ml-1 | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 4.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 7.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 9.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 13.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 14.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 15.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 16.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 17.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 18.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 25.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 43.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 76.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 97.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 132.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 149.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 153.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 155.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 171.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 177.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 184.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Ratio ED50 | 264.0 | None | 10.1021/np50091a005 |
| None | Unchecked | Selectivity Index | 21.0 | None | 10.1021/np980144f |
| None | Unchecked | Selectivity Index | 49.0 | None | 10.1021/np980144f |