CHEBI:5858 - icaceine

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ChEBI Name icaceine
ChEBI ID CHEBI:5858
Definition A diterpene alkaloid that is 6,18:14,16-diepoxypimar-7-en-18-one substituted by a hydroxy group at position 3 and a dimethyl amino group at position 15. It is isolated from Icacina guessfeldtii.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C22H33NO4
Net Charge 0
Average Mass 375.50170
Monoisotopic Mass 375.24096
InChI InChI=1S/C22H33NO4/c1-20-9-7-16(24)22(3)17(20)14(27-19(22)25)10-12-13(20)6-8-21(2)15(23(4)5)11-26-18(12)21/h10,13-18,24H,6-9,11H2,1-5H3/t13?,14-,15?,16+,17-,18?,20-,21?,22+/m1/s1
InChIKey MRVMMDQTZLIFLF-IQTYJBGDSA-N
SMILES [H][C@@]12OC(=O)[C@@]3(C)[C@@H](O)CC[C@](C)(C4CCC5(C)C(COC5C4=C1)N(C)C)[C@@]23[H]
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.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing icaceine (CHEBI:5858) has role metabolite (CHEBI:25212)
icaceine (CHEBI:5858) is a diterpene alkaloid (CHEBI:23847)
icaceine (CHEBI:5858) is a diterpene lactone (CHEBI:49193)
icaceine (CHEBI:5858) is a pimarane diterpenoid (CHEBI:49192)
icaceine (CHEBI:5858) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
(3β,6β,9ξ,13ξ)-15-(dimethylamino)-3-hydroxy-6,18:14,16-diepoxypimar-7-en-18-one
Manual Xrefs Databases
C00001645 KNApSAcK
C08689 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
6533368 Reaxys Registry Number Reaxys
74991-71-2 CAS Registry Number KEGG COMPOUND
Last Modified
28 July 2014