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dysidine
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 muM.


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > dysidine [CHEBI:65816]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 phospholipase A2 inhibitor [CHEBI:50469] (3) 
 dysidine [CHEBI:65816] (1)
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 dysidine [CHEBI:65816] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 enol [CHEBI:33823] (52) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 organic amino compound [CHEBI:50047] (2472) 
 secondary amino compound [CHEBI:50995] (110) 
 dysidine [CHEBI:65816] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 enol [CHEBI:33823] (52) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 benzoquinones [CHEBI:22729] (30) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 sulfur molecular entity [CHEBI:26835] (1541) 
 organosulfur compound [CHEBI:33261] (1005) 
 organosulfonic acid [CHEBI:33551] (119) 
 dysidine [CHEBI:65816] (1)
 sulfur oxoacid derivative [CHEBI:33424] (628) 
 sulfonic acid derivative [CHEBI:33552] (393) 
 organosulfonic acid [CHEBI:33551] (119) 
 dysidine [CHEBI:65816] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organosulfur compound [CHEBI:33261] (1005) 
 organosulfonic acid [CHEBI:33551] (119) 
 dysidine [CHEBI:65816] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 benzoquinones [CHEBI:22729] (30) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 lipid [CHEBI:18059] (3532) 
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 sesquiterpenoid [CHEBI:26658] (209) 
 dysidine [CHEBI:65816] (1)
 isoprenoid [CHEBI:24913] (1402) 
 terpenoid [CHEBI:26873] (1099) 
 sesquiterpenoid [CHEBI:26658] (209) 
 dysidine [CHEBI:65816] (1)
 heteroorganic entity [CHEBI:33285] (15197) 
 organonitrogen compound [CHEBI:35352] (6705) 
 organic amino compound [CHEBI:50047] (2472) 
 secondary amino compound [CHEBI:50995] (110) 
 dysidine [CHEBI:65816] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organosulfur compound [CHEBI:33261] (1005) 
 organosulfonic acid [CHEBI:33551] (119) 
 dysidine [CHEBI:65816] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 benzoquinones [CHEBI:22729] (30) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 enol [CHEBI:33823] (52) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 quinone [CHEBI:36141] (209) 
 benzoquinones [CHEBI:22729] (30) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 organic amino compound [CHEBI:50047] (2472) 
 secondary amino compound [CHEBI:50995] (110) 
 dysidine [CHEBI:65816] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 benzoquinones [CHEBI:22729] (30) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 organic molecule [CHEBI:72695] (11399) 
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 benzoquinones [CHEBI:22729] (30) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 enol [CHEBI:33823] (52) 
 2-hydroxy-1,4-benzoquinones [CHEBI:67273] (3) 
 dysidine [CHEBI:65816] (1)
 oxoacid derivative [CHEBI:33241] (3254) 
 sulfur oxoacid derivative [CHEBI:33424] (628) 
 sulfonic acid derivative [CHEBI:33552] (393) 
 organosulfonic acid [CHEBI:33551] (119) 
 dysidine [CHEBI:65816] (1)
ChEBI Compound Accession Identifier  [CHEBI:65816]
ChEBI Compound Description  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 muM.
ChEBI Compound Identification Number  65816
ChEBI InChI Value  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
ChEBI InChIKey Value  HHKUTKBQEPDLMV-CIVZFWGOSA-N
ChEBI Compound Name  dysidine
ChEBI SMILES Value  [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
ChEBI Substance ID  160645210
ChEBI URL  ChEBI:65816
ChemSpider ID  10214288
Ontomatica Chemical Accession Key (OnChAKey)  HHKUTKBQEPDLMV_CIVZFWGOSA_N_000_000000
PubChem Compound ID  10321583