CHEBI:65816 - dysidine

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ChEBI Name dysidine
ChEBI ID CHEBI:65816
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C23H33NO6S
Net Charge 0
Average Mass 451.57600
Monoisotopic Mass 451.20286
InChI InChI=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
InChIKey HHKUTKBQEPDLMV-CIVZFWGOSA-N
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
Metabolite of Species Details
Dysidea (NCBI:txid190526) 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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
8810146 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11374954 PubMed citation Europe PMC
19091557 PubMed citation Europe PMC
19262557 PubMed citation Europe PMC
Last Modified
07 September 2017