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CHEBI:65816 - dysidine

Default Structure
ChEBI IDCHEBI:65816
ChEBI Namedysidine
Stars
DefinitionA sesquiterpenoid isolated from the sponge Dysidea sp. that is 5-amino-2-hydroxy-3-methyl-1,4-benzoquinone in which one of the hydrogens of the methyl group is replaced by a 1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-yl group and one of the hydrogens attached to the nitrogen is replaced by a 2-sulfoethyl group. Dysidine selectively inhibits human synovial phospholipase A2 (EC 3.1.1.4) with an IC50 = 2.0 μM.
Last Modified7 September 2017
DownloadsMolfile
FormulaC23H33NO6S
Net Charge0
Average Mass451.585
Monoisotopic Mass451.20286
SMILES[H][C@@]12CCC=C(C)[C@@]1(C)CC[C@](C)(CC1=C(O)C(=O)C=C(NCCS(=O)(=O)O)C1=O)[C@@H]2C
InChIInChI=1S/C23H33NO6S/c1-14-6-5-7-17-15(2)22(3,8-9-23(14,17)4)13-16-20(26)18(12-19(25)21(16)27)24-10-11-31(28,29)30/h6,12,15,17,24,27H,5,7-11,13H2,1-4H3,(H,28,29,30)/t15-,17+,22-,23-/m1/s1
InChIKeyHHKUTKBQEPDLMV-CIVZFWGOSA-N
Species of MetaboliteComponentSourceComments
Dysidea (ncbitaxon:190526) - PubMed (11374954)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 3.1.1.4 (phospholipase A2) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).
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)
dysidine (CHEBI:65816) has role EC 3.1.1.4 (phospholipase A2) inhibitor (CHEBI:50469)
dysidine (CHEBI:65816) has role metabolite (CHEBI:25212)
dysidine (CHEBI:65816) is a monohydroxy-1,4-benzoquinones (CHEBI:67273)
dysidine (CHEBI:65816) is a octahydronaphthalenes (CHEBI:138397)
dysidine (CHEBI:65816) is a organosulfonic acid (CHEBI:33551)
dysidine (CHEBI:65816) is a secondary amino compound (CHEBI:50995)
dysidine (CHEBI:65816) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
2-[(4-hydroxy-3,6-dioxo-5-{[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-yl]methyl}cyclohexa-1,4-dien-1-yl)amino]ethanesulfonic acid
Registry NumbersSources
Reaxys:8810146Reaxys
Citations