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CHEBI:65988 - gummiferaoside C

ChEBI IDCHEBI:65988
ChEBI Namegummiferaoside C
Stars
DefinitionA triterpenoid saponin isolated from the roots of of the Madagascan plant Albizia gummifera and has been shown to exhibit cytotoxicity against human ovarian cancer cell line.
Last Modified20 January 2014
DownloadsMolfile
FormulaC113H178O50
Net Charge0
Average Mass2336.617
Monoisotopic Mass2335.13859
SMILES[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO[C@@H]3O[C@H](C)[C@H](O)[C@H](O)[C@H]3O)O[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])CC=C5[C@]6([H])CC(C)(C)[C@@H](OC(=O)/C(C)=C/CC[C@@](C)(C=C)O[C@@H]7O[C@H](C)[C@@H](OC(=O)/C(C)=C/CC[C@](C)(C=C)O[C@@H]8O[C@H](C)[C@@H](OC(=O)/C(C)=C/CC[C@](C)(C=C)O[C@@H]9O[C@H](C)[C@@H](O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)C[C@]6(C(=O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@@]6([H])O[C@H](C)[C@@H](O[C@]7([H])OC[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@@H]6O)[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/C113H178O50/c1-22-107(16,161-99-83(135)73(125)67(119)51(8)146-99)36-26-29-48(5)93(140)155-88-53(10)149-101(86(138)79(88)131)163-109(18,24-3)37-27-30-49(6)94(141)156-87-52(9)148-100(85(137)78(87)130)162-108(17,23-2)35-25-28-47(4)92(139)153-65-42-113(104(142)160-103-91(75(127)70(122)59(44-115)151-103)158-97-84(136)77(129)89(54(11)147-97)157-96-80(132)68(120)57(116)45-143-96)56(40-105(65,12)13)55-31-32-62-110(19)38-34-64(106(14,15)61(110)33-39-111(62,20)112(55,21)41-63(113)117)154-102-90(159-98-82(134)74(126)69(121)58(43-114)150-98)76(128)71(123)60(152-102)46-144-95-81(133)72(124)66(118)50(7)145-95/h22-24,28-31,50-54,56-91,95-103,114-138H,1-3,25-27,32-46H2,4-21H3/b47-28+,48-29+,49-30+/t50-,51-,52-,53-,54-,56+,57-,58-,59-,60-,61+,62-,63-,64+,65+,66+,67-,68+,69-,70-,71-,72+,73+,74+,75+,76+,77-,78-,79-,80-,81-,82-,83-,84+,85-,86-,87-,88-,89-,90-,91-,95-,96+,97-,98+,99+,100+,101+,102+,103+,107+,108-,109+,110+,111-,112-,113-/m1/s1
InChIKeyMGIDRSGNPPWHNL-AQNAKNDQSA-N
Species of MetaboliteComponentSourceComments
Albizia gummifera (IPNI:473259-1) root (BTO:0001188) PubMed (17263578)
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
gummiferaoside C (CHEBI:65988) has parent hydride oleanane (CHEBI:36481)
gummiferaoside C (CHEBI:65988) has role antineoplastic agent (CHEBI:35610)
gummiferaoside C (CHEBI:65988) has role plant metabolite (CHEBI:76924)
gummiferaoside C (CHEBI:65988) is a enoate ester (CHEBI:51702)
gummiferaoside C (CHEBI:65988) is a pentacyclic triterpenoid (CHEBI:25872)
gummiferaoside C (CHEBI:65988) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name 
β-D-xylopyranosyl-(1→4)-6-deoxy-α-D-mannopyranosyl-(1→2)-1-O-[(3β,16α,21β)-21-({(2E,6S)-6-[(6-deoxy-4-O-{(2E,6R)-6-[(6-deoxy-4-O-{(2E,6R)-6-[(6-deoxy-β-D-glucopyranosyl)oxy]-2,6-dimethylocta-2,7-dienoyl}-β-D-glucopyranosyl)oxy]-2,6-dimethylocta-2,7-dienoyl}-β-D-glucopyranosyl)oxy]-2,6-dimethylocta-2,7-dienoyl}oxy)-3-{[6-deoxy-β-D-galactopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl]oxy}-16-hydroxy-28-oxoolean-12-en-28-yl]-β-D-glucopyranose
Registry NumbersSources
Reaxys:11058835Reaxys
Citations