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CHEBI:67561 - paraminabeolide B

ChEBI IDCHEBI:67561
ChEBI Nameparaminabeolide B
Stars
DefinitionA withanolide that is 22,26-epoxyergosta-1,4-diene substituted by an acetyloxy group at position 18 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
FormulaC30H42O5
Net Charge0
Average Mass482.661
Monoisotopic Mass482.30322
SMILES[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@@]1(COC(C)=O)[C@@]2([H])CC[C@]1([H])[C@H](C)[C@@]1([H])C[C@H](C)[C@H](C)C(=O)O1
InChIInChI=1S/C30H42O5/c1-17-14-27(35-28(33)18(17)2)19(3)24-8-9-26-23-7-6-21-15-22(32)10-12-29(21,5)25(23)11-13-30(24,26)16-34-20(4)31/h10,12,15,17-19,23-27H,6-9,11,13-14,16H2,1-5H3/t17-,18-,19-,23+,24+,25-,26-,27+,29-,30-/m0/s1
InChIKeyCJVKACGPAQCXAA-RXQWXACOSA-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 B (CHEBI:67561) has role coral metabolite (CHEBI:76498)
paraminabeolide B (CHEBI:67561) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
paraminabeolide B (CHEBI:67561) is a 3-oxo-Δ1,Δ4-steroid (CHEBI:77166)
paraminabeolide B (CHEBI:67561) is a acetate ester (CHEBI:47622)
paraminabeolide B (CHEBI:67561) is a ergostanoid (CHEBI:50403)
paraminabeolide B (CHEBI:67561) is a steroid ester (CHEBI:47880)
paraminabeolide B (CHEBI:67561) is a withanolide (CHEBI:74716)
paraminabeolide B (CHEBI:67561) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(22R,25S)-3,26-dioxo-22,26-epoxyergosta-1,4-dien-18-yl acetate
Registry NumbersSources
Reaxys:21534305Reaxys
Citations