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CHEBI:67497 - gordonoside I

ChEBI IDCHEBI:67497
ChEBI Namegordonoside I
Stars
DefinitionA triterpenoid saponin that is 3,16,28-trihydroxyolean-12-en-22-yl (2Z)-2-methylbut-2-enoate attached to a tetrasaccharide residue at position 3 via a glycosidic linkage. Isolated from the stems of Gordonia chrysandra, it exhibits a strong inhibitory effect on nitric oxide production.
Last Modified9 January 2014
DownloadsMolfile
FormulaC57H90O24
Net Charge0
Average Mass1159.323
Monoisotopic Mass1158.58220
SMILES[H][C@@]1(O[C@@H]2[C@@H](O[C@]3([H])OC[C@H](O)[C@H](O)[C@H]3O[C@]3([H])OC[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@@H](C(=O)O)O[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])CC=C5[C@]6([H])CC(C)(C)C[C@H](OC(=O)/C(C)=C\C)[C@]6(CO)[C@H](O)C[C@@]5(C)[C@]4(C)CC[C@@]3([H])C2(C)C)O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C57H90O24/c1-10-24(2)47(72)76-34-19-52(3,4)17-26-25-11-12-31-54(7)15-14-33(53(5,6)30(54)13-16-55(31,8)56(25,9)18-32(62)57(26,34)23-59)77-51-45(81-49-40(68)38(66)37(65)29(20-58)75-49)42(41(69)43(79-51)46(70)71)78-50-44(36(64)28(61)22-74-50)80-48-39(67)35(63)27(60)21-73-48/h10-11,26-45,48-51,58-69H,12-23H2,1-9H3,(H,70,71)/b24-10-/t26-,27+,28-,29+,30-,31+,32+,33-,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+,48-,49-,50-,51+,54-,55+,56+,57-/m0/s1
InChIKeyBHKKNGSHLSYLPN-KOYGLFPPSA-N
Species of MetaboliteComponentSourceComments
Gordonia chrysandra (ncbitaxon:182314) stem (BTO:0001300) PubMed (21473609) 95% ethanolic extract of air-dried stems
Roles Classification
Biological Roles:
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.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
gordonoside I (CHEBI:67497) has functional parent angelic acid (CHEBI:36431)
gordonoside I (CHEBI:67497) has parent hydride oleanane (CHEBI:36481)
gordonoside I (CHEBI:67497) has role anti-inflammatory agent (CHEBI:67079)
gordonoside I (CHEBI:67497) has role plant metabolite (CHEBI:76924)
gordonoside I (CHEBI:67497) is a pentacyclic triterpenoid (CHEBI:25872)
gordonoside I (CHEBI:67497) is a tetrasaccharide derivative (CHEBI:63567)
gordonoside I (CHEBI:67497) is a triterpenoid saponin (CHEBI:61778)
gordonoside I (CHEBI:67497) is a β-D-glucosiduronic acid (CHEBI:15341)
IUPAC Name 
(3β,16α,22α)-16,28-dihydroxy-22-{[(2Z)-2-methylbut-2-enoyl]oxy}olean-12-en-3-yl β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranosiduronic acid
Synonym  Source
3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucuronopyranosyl-22α-angeloyloxyolean-12-ene-16α,28-diolChEBI
Registry NumbersSources
Reaxys:21534294Reaxys
Citations