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CHEBI:67562 - paraminabeolide C

ChEBI IDCHEBI:67562
ChEBI Nameparaminabeolide C
Stars
DefinitionA withanolide that is 23,26-epoxyergosta-1,4-diene substituted by an acetyloxy group at position 18, a hydroxy group at position 22 and oxo groups at positions 3 and 26. Isolated from a Formosan soft coral Paraminabea acronocephala, it has been found to inhibit the accumulation of the pro-inflammatory iNOS protein.
Last Modified30 January 2014
DownloadsMolfile
FormulaC30H42O6
Net Charge0
Average Mass498.660
Monoisotopic Mass498.29814
SMILES[H][C@@]1([C@@H](O)[C@@H](C)[C@@]2([H])CC[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])CC[C@@]32COC(C)=O)OC(=O)[C@H](C)[C@H]1C
InChIInChI=1S/C30H42O6/c1-16-17(2)28(34)36-27(16)26(33)18(3)23-8-9-25-22-7-6-20-14-21(32)10-12-29(20,5)24(22)11-13-30(23,25)15-35-19(4)31/h10,12,14,16-18,22-27,33H,6-9,11,13,15H2,1-5H3/t16-,17-,18+,22-,23-,24+,25+,26+,27-,29+,30+/m1/s1
InChIKeyCFLDASSGYNALJR-DYJDMTRPSA-N
Species of MetaboliteComponentSourceComments
Paraminabea acronocephala (WORMS:290662) - PubMed (21425785) Ethanolic extract of minced frozen bodies
Roles Classification
Biological Roles:
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
coral metabolite  Any animal metabolite produced during a metabolic reaction in corals (marine invertebrates).
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
paraminabeolide C (CHEBI:67562) has role coral metabolite (CHEBI:76498)
paraminabeolide C (CHEBI:67562) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
paraminabeolide C (CHEBI:67562) is a 3-oxo-Δ1,Δ4-steroid (CHEBI:77166)
paraminabeolide C (CHEBI:67562) is a acetate ester (CHEBI:47622)
paraminabeolide C (CHEBI:67562) is a ergostanoid (CHEBI:50403)
paraminabeolide C (CHEBI:67562) is a secondary alcohol (CHEBI:35681)
paraminabeolide C (CHEBI:67562) is a steroid ester (CHEBI:47880)
paraminabeolide C (CHEBI:67562) is a withanolide (CHEBI:74716)
paraminabeolide C (CHEBI:67562) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(22S,23R,25R)-22-hydroxy-3,26-dioxo-23,26-epoxyergosta-1,4-dien-18-yl acetate
Registry NumbersSources
Reaxys:21534309Reaxys
Citations