CHEBI:67503 - gordonoside O

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ChEBI Name gordonoside O
ChEBI ID CHEBI:67503
Definition A triterpenoid saponin that has 3,16-dihydroxyolean-12-en-28-oic acid as the aglycone. Isolated from the stems of Gordonia chrysandra, it exhibits a strong inhibitory effect on nitric oxide production.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C58H92O28
Net Charge 0
Average Mass 1237.33430
Monoisotopic Mass 1236.57751
InChI InChI=1S/C58H92O28/c1-53(2)14-15-58(52(76)86-49-40(72)37(69)35(67)27(19-60)80-49)23(16-53)22-8-9-29-55(5)12-11-31(54(3,4)28(55)10-13-56(29,6)57(22,7)17-30(58)63)81-51-45(85-48-39(71)36(68)34(66)26(18-59)79-48)42(41(73)43(83-51)46(74)75)82-50-44(33(65)25(62)21-78-50)84-47-38(70)32(64)24(61)20-77-47/h8,23-45,47-51,59-73H,9-21H2,1-7H3,(H,74,75)/t23-,24+,25-,26+,27+,28-,29+,30+,31-,32-,33-,34-,35+,36-,37-,38+,39+,40+,41-,42-,43-,44+,45+,47-,48-,49-,50-,51+,55-,56+,57+,58+/m0/s1
InChIKey GNQHWAAORKJVMT-UFJWLZDESA-N
SMILES CC1(C)CC[C@@]2([C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O[C@@H]7OC[C@H](O)[C@H](O)[C@H]7O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)C(O)=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Gordonia chrysandra (NCBI:txid182314) Found in stem (BTO:0001300). 95% ethanolic extract of air-dried stems See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing gordonoside O (CHEBI:67503) has parent hydride oleanane (CHEBI:36481)
gordonoside O (CHEBI:67503) has role anti-inflammatory agent (CHEBI:67079)
gordonoside O (CHEBI:67503) has role plant metabolite (CHEBI:76924)
gordonoside O (CHEBI:67503) is a β-D-glucosiduronic acid (CHEBI:15341)
gordonoside O (CHEBI:67503) is a carboxylic ester (CHEBI:33308)
gordonoside O (CHEBI:67503) is a pentacyclic triterpenoid (CHEBI:25872)
gordonoside O (CHEBI:67503) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
1-O-[(3β,16α)-3-{[β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranuronosyl]oxy}-16-hydroxy-28-oxoolean-12-en-28-yl]-β-D-glucopyranose
Registry Number Type Source
21534297 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21473609 PubMed citation Europe PMC
Last Modified
09 January 2014