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CHEBI:65816 - dysidine

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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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