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Gelsemium alkaloids
Description:
Alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.
Ancestors:
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rankinidineCas Number: 106466-66-4 Compound CID: 6439112IUPAC Name: (7Z)-7-ethylidene-1'-methoxyspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-oneSMILES: CC=C1CNC2CC3(C4CC1C2CO4)C5=CC=CC=C5N(C3=O)OCInChIKey: ZXRGGMATGWCUBP-KGVSQERTSA-NInChI: InChI=1S/C20H24N2O3/c1-3-12-10-21-16-9-20(18-8-13(12)14(16)11-25-18)15-6-4-5-7-17(15)22(24-2)19(20)23/h3-7,13-14,16,18,21H,8-11H2,1-2H3/b12-3+
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HumantenineCas Number: 82375-29-9 Compound CID: 44593672IUPAC Name: (1R,2S,4S,7Z,8R,9S)-7-ethylidene-1'-methoxy-5-methylspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-oneSMILES: CC=C1CN(C2CC3(C4CC1C2CO4)C5=CC=CC=C5N(C3=O)OC)CInChIKey: SJKRPUOXUNOPOP-YDAOCWKESA-NInChI: show more
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GelsemineCas Number: 509-15-9Formula: C20H22N2O2 Molecular Weight: 322.4IUPAC Name: (1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-oneSMILES: CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=CInChIKey: NFYYATWFXNPTRM-QJICHLCESA-NInChI: show moreSynonyms: GELSEMINE|509-15-9|Gelsemin|5Y13A78Z72|NSC-21729|UNII-5Y13A78Z72|HSDB 3488|gelsemine free base|(+)-Gelsemine|EINECS 2...
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GelsemineCas Number: 509-15-9Formula: C20H22N2O2 Molecular Weight: 322.4IUPAC Name: (1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-4'-methylspiro[1H-indole-3,7'-9-oxa-4-azatetracyclo[6.3.1.02,6.05,11]dodecane]-2-oneSMILES: CN1CC2(C3CC4C5(C2C1C3CO4)C6=CC=CC=C6NC5=O)C=CInChIKey: NFYYATWFXNPTRM-QJICHLCESA-NInChI: show moreSynonyms: s9294 | GELSEMINE [MI] | NSC 21729 | Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one...
