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CHEBI:27776 - geissospermine

ChEBI IDCHEBI:27776
ChEBI Namegeissospermine
Stars
DefinitionA indole alkaloid comprising two indole-derived polycyclic moieties joined by a cyclic ether linkage.
Secondary ChEBI IDsCHEBI:5284, CHEBI:24203
Last Modified30 March 2015
DownloadsMolfile
FormulaC40H48N4O3
Net Charge0
Average Mass632.849
Monoisotopic Mass632.37264
SMILES[H][C@@]1(CC)CN2CC[C@]34c5ccccc5N5[C@@]3([H])[C@@]([H])(CO[C@@]5([H])[C@]([H])(C(=O)OC)[C@@]3([H])C[C@@]5([H])c6nc7ccccc7c6CCN5C/C3=C/C)[C@@]1([H])C[C@]24[H]
InChIInChI=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
InChIKeyISDWYSGTYITCHG-OCNKQYNFSA-N
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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
GeissospermineKEGG COMPOUND
Manual XrefsDatabases
C00001732KNApSAcK
C09200KEGG COMPOUND
Registry NumbersSources
Reaxys:76217Reaxys
CAS:427-01-0ChemIDplus
CAS:427-01-0KEGG COMPOUND
Citations