CHEBI:66690 - melemeleone B

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ChEBI Name melemeleone B
ChEBI ID CHEBI:66690
Definition A sesquiterpenoid with a quinone and taurine functionality. It is isolated from the sponge Dysidea avara, and exhibits inhibitory activity against tyrosine kinase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000100090361
Download Molfile XML SDF
Formula C23H33NO5S
Net Charge 0
Average Mass 435.57700
Monoisotopic Mass 435.20794
InChI InChI=1S/C23H33NO5S/c1-15-6-5-7-21-22(15,3)9-8-16(2)23(21,4)14-17-12-20(26)18(13-19(17)25)24-10-11-30(27,28)29/h6,12-13,16,21,24H,5,7-11,14H2,1-4H3,(H,27,28,29)/t16-,21+,22+,23+/m0/s1
InChIKey DTNJUMSQZGAJQJ-RAKGIWIYSA-N
SMILES [H][C@@]12CCC=C(C)[C@@]1(C)CC[C@H](C)[C@@]2(C)CC1=CC(=O)C(NCCS(O)(=O)=O)=CC1=O
Metabolite of Species Details
Dysidea avara (NCBI:txid196820) See: DOI
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): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing melemeleone B (CHEBI:66690) has functional parent taurine (CHEBI:15891)
melemeleone B (CHEBI:66690) has role metabolite (CHEBI:25212)
melemeleone B (CHEBI:66690) has role tyrosine kinase inhibitor (CHEBI:38637)
melemeleone B (CHEBI:66690) is a 1,4-benzoquinones (CHEBI:132124)
melemeleone B (CHEBI:66690) is a amino sulfonic acid (CHEBI:37793)
melemeleone B (CHEBI:66690) is a octahydronaphthalenes (CHEBI:138397)
melemeleone B (CHEBI:66690) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
2-[(3,6-dioxo-4-{[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]methyl}cyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid
Registry Number Type Source
5887590 Reaxys Registry Number Reaxys
Last Modified
07 September 2017
General Comment
2013-04-05 J. Org. Chem. (1992), 57, 6604-6607