CHEBI:27776 - geissospermine

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ChEBI Name geissospermine
ChEBI ID CHEBI:27776
Definition A indole alkaloid comprising two indole-derived polycyclic moieties joined by a cyclic ether linkage.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24203, CHEBI:5284
Supplier Information
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Formula C40H48N4O3
Net Charge 0
Average Mass 632.83410
Monoisotopic Mass 632.37264
InChI InChI=1S/C40H48N4O3/c1-4-23-21-43-17-15-40-30-11-7-9-13-32(30)44-37(40)29(27(23)19-34(40)43)22-47-38(44)35(39(45)46-3)28-18-33-36-26(14-16-42(33)20-24(28)5-2)25-10-6-8-12-31(25)41-36/h5-13,23,27-29,33-35,37-38,41H,4,14-22H2,1-3H3/b24-5-/t23-,27+,28+,29+,33+,34+,35-,37+,38+,40-/m1/s1
InChIKey ISDWYSGTYITCHG-OCNKQYNFSA-N
SMILES [H][C@@]1(CC)CN2CC[C@@]34c5ccccc5N5[C@@]([H])(OC[C@@]([H])([C@@]1([H])C[C@]23[H])[C@@]45[H])[C@]([H])(C(=O)OC)[C@@]1([H])C[C@]2([H])N(CCc3c2[nH]c2ccccc32)C\C1=C\C
Roles Classification
Biological Role(s): EC 3.1.1.7 (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing geissospermine (CHEBI:27776) has parent hydride corynan (CHEBI:35653)
geissospermine (CHEBI:27776) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
geissospermine (CHEBI:27776) is a indole alkaloid (CHEBI:38958)
geissospermine (CHEBI:27776) is a methyl ester (CHEBI:25248)
geissospermine (CHEBI:27776) is a organic heteropentacyclic compound (CHEBI:38164)
geissospermine (CHEBI:27776) is a organic heterotetracyclic compound (CHEBI:38163)
IUPAC Name
methyl (2R)-[(3aR,9S,11aS,11bS,12S,13aS,14S)-14-ethyl-2,3,11a,12,13,13a-hexahydro-11H,11bH-1,12-ethano[1,3]oxazino[3,4,5-lm]pyrrolo[2,3-d]carbazol-9-yl][(2R,3E,12bS)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]acetate
Synonym Source
Geissospermine KEGG COMPOUND
Manual Xrefs Databases
C00001732 KNApSAcK
C09200 KEGG COMPOUND
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Registry Numbers Types Sources
427-01-0 CAS Registry Number KEGG COMPOUND
427-01-0 CAS Registry Number ChemIDplus
76217 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
13231363 PubMed citation Europe PMC
13685183 PubMed citation Europe PMC
13685184 PubMed citation Europe PMC
13863306 PubMed citation Europe PMC
14435279 PubMed citation Europe PMC
19463267 PubMed citation Europe PMC
20844909 PubMed citation Europe PMC
Last Modified
30 March 2015