CHEBI:66017 - hispidospermidin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name hispidospermidin
ChEBI ID CHEBI:66017
Definition A bridged compound with a trimethylspermidine side chain. It is isolated from Chaetosphaeronema hispidulum (Cda) Moesz NR 7127 and has been shown to exhibit inhibitory activity against phosphatidylinositol-specific phospholipase C (PLC).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C25H47N3O
Net Charge 0
Average Mass 405.66020
Monoisotopic Mass 405.37191
InChI InChI=1S/C25H47N3O/c1-19-10-11-21-24(3)22(20-18-25(19,21)13-12-23(20,2)29-24)26-14-7-8-16-28(6)17-9-15-27(4)5/h19-22,26H,7-18H2,1-6H3/t19-,20-,21-,22+,23-,24+,25+/m1/s1
InChIKey JIRJLWLQLDLWSW-XNDBBLGPSA-N
SMILES [H][C@]12C[C@]34CC[C@@]1(C)O[C@](C)([C@H]2NCCCCN(C)CCCN(C)C)[C@@]3([H])CC[C@H]4C
Metabolite of Species Details
Chaetosphaeronema hispidulum (NCBI:txid565418) of strain NR 7127 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
An EC 3.1.4.* (phosphoric diester hydrolase) inhibitor that interferes with the action of phosphatidylinositol-specific phospholipase C (EC 3.1.4.11).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing hispidospermidin (CHEBI:66017) has role EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor (CHEBI:64763)
hispidospermidin (CHEBI:66017) has role metabolite (CHEBI:25212)
hispidospermidin (CHEBI:66017) is a bridged compound (CHEBI:35990)
hispidospermidin (CHEBI:66017) is a cyclic ether (CHEBI:37407)
hispidospermidin (CHEBI:66017) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
N-[3-(dimethylamino)propyl]-N-methyl-N'-[(3R,3aS,6R,7R,8S,9S,9aS)-3,6,9-trimethyldecahydro-6,9-epoxy-3a,7-methanocyclopenta[8]annulen-8-yl]butane-1,4-diamine
Synonym Source
(−)-hispidospermidin ChEBI
Manual Xrefs Databases
EP0600342 Patent
US5430050 Patent
View more database links
Registry Number Type Source
6848749 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
7509786 PubMed citation Europe PMC
7509787 PubMed citation Europe PMC
Last Modified
20 February 2013