| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H24N2O4 |
| Molecular Weight | 368.4263 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CC[C@]4([C@@H]3C[C@H]12)C(=O)NC5=C4C=CC=C5
InChI
InChIKey=JMIAZDVHNCCPDM-PFDNRQJHSA-N
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18-,21-/m0/s1
| Molecular Formula | C21H24N2O4 |
| Molecular Weight | 368.4263 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Isopteropodine is an Uncaria pentacyclic oxindol alkaloid. It is exhibited antibacterial activity against Gram-positive bacteria. The moderate anti-proliferative effect of isopteropodine was demonstrated on the acute lymphoblastic leukaemia cells. Isopteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte but further studies are necessary to elucidate the exact mechanism by which isopteropodine positively modulates muscarinic M1 and 5-HT2 receptor functions. Isopteropodine blocked the impairment of passive avoidance performance caused by the nicotinic receptor antagonist mecamylamine and the N-methyl-D-aspartate (NMDA) receptor antagonist (+/-)-3-(2-carboxypiperazin-4-yl)- propyl-1-phosphonic acid (CPP) in mouse model. Moreover, it is possible that the glutamatergic systems are implicated in the anti-amnesic effect of isopteropodine.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
The Isopteropodine showed moderate cytotoxicity to several mammalian cell lines (BALB/c 3T3 (mouse fibroblasts); H460 (human non-small cell lung carcinoma); MEI8O (human cervical carcinoma); DU145 (human prostate carcinoma); LSR (mouse reticular lymphosarcoma); C678 (mouse C3H stomach carcinoma), with IC50 values ranging from 17—51 ug/mL. These activities are significantly less than those shown by camptothecin and streptonigrin.
