Molecule ID: 10321583

IUPAC Name: 2-[[5-[[(1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,3,4,7,8,8a-hexahydronaphthalen-2-yl]methyl]-6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl]amino]ethanesulfonic acid

Description: The molecule is 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. It has a role as a metabolite and an EC 3.1.1.4 (phospholipase A2) inhibitor. It is a secondary amino compound, an organosulfonic acid, a sesquiterpenoid, a member of monohydroxy-1,4-benzoquinones and a member of octahydronaphthalenes.

SMILES: CC1=CCC[C@H]2[C@@H](C)[C@@](C)(CC3=C(O)C(NCCS(=O)(=O)O)=CC(=O)C3=O)CC[C@]12C

SELFIES: [C][C][=C][C][C][C@H1][C@@H1][Branch1][C][C][C@@][Branch1][C][C][Branch2][Ring1][=C][C][C][=C][Branch1][C][O][C][Branch1][N][N][C][C][S][=Branch1][C][=O][=Branch1][C][=O][O][=C][C][=Branch1][C][=O][C][Ring1][#C][=O][C][C][C@][Ring2][Ring1][=N][Ring2][Ring1][=Branch2][C]

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/h6,12,15,17,24,26H,5,7-11,13H2,1-4H3,(H,28,29,30)/t15-,17+,22-,23-/m1/s1

Molecular Properties:
- Polar Surface Area: 129.0 Ų
- LogP: 3.6