gummiferaoside B (CHEBI:65987)

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CHEBI:65987 - gummiferaoside B

ChEBI ID	CHEBI:65987
ChEBI Name	gummiferaoside B
Stars
Definition	A 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 Modified	20 January 2014
Downloads	Molfile

Formula	C102H162O48
Net Charge	0
Average Mass	2156.370
Monoisotopic Mass	2155.02356
SMILES	[H][C@@]1(O[C@H]2[C@H](OC[C@H]3O[C@@]([H])(O[C@H]4CC[C@]5(C)[C@@]6([H])CC=C7[C@]8([H])CC(C)(C)[C@@H](OC(=O)/C(C)=C/CC[C@@](C)(C=C)O[C@@H]9O[C@H](C)[C@@H](OC(=O)/C(C)=C/CC[C@](C)(C=C)O[C@@H]%10O[C@H](C)[C@@H](O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)C[C@]8(C(=O)O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O[C@@]8([H])O[C@H](C)[C@@H](O[C@]9([H])OC[C@@H](O)[C@H](O)[C@H]9O)[C@H](O)[C@@H]8O)[C@H](O)C[C@@]7(C)[C@]6(C)CC[C@@]5([H])C4(C)C)[C@H](O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@@H]3O)O[C@H](C)[C@H](O)[C@@H]2O)OC[C@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C102H162O48/c1-18-97(13,149-89-75(125)65(115)58(108)42(5)134-89)29-21-23-41(4)84(129)143-78-44(7)137-90(77(127)71(78)121)150-98(14,19-2)28-20-22-40(3)83(128)141-57-34-102(94(130)148-93-82(68(118)63(113)51(36-104)139-93)146-87-76(126)70(120)79(45(8)136-87)144-85-72(122)60(110)48(105)37-131-85)47(32-95(57,9)10)46-24-25-54-99(15)30-27-56(96(11,12)53(99)26-31-100(54,16)101(46,17)33-55(102)107)142-92-81(147-88-74(124)66(116)62(112)50(35-103)138-88)69(119)64(114)52(140-92)39-133-91-80(67(117)59(109)43(6)135-91)145-86-73(123)61(111)49(106)38-132-86/h18-19,22-24,42-45,47-82,85-93,103-127H,1-2,20-21,25-39H2,3-17H3/b40-22+,41-23+/t42-,43-,44-,45-,47+,48-,49+,50-,51-,52-,53+,54-,55-,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-,85+,86+,87-,88+,89+,90+,91-,92+,93+,97+,98-,99+,100-,101-,102-/m1/s1
InChIKey	WWTIDCRMMJEMDR-WLGZQPPQSA-N

Species of Metabolite	Component	Source	Comments
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 B (CHEBI:65987) has parent hydride oleanane (CHEBI:36481)
	gummiferaoside B (CHEBI:65987) has role antineoplastic agent (CHEBI:35610)
	gummiferaoside B (CHEBI:65987) has role plant metabolite (CHEBI:76924)
	gummiferaoside B (CHEBI:65987) is a enoate ester (CHEBI:51702)
	gummiferaoside B (CHEBI:65987) is a pentacyclic triterpenoid (CHEBI:25872)
	gummiferaoside B (CHEBI:65987) 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)-3-{[α-L-arabinopyranosyl-(1→2)-6-deoxy-β-D-galactopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl]oxy}-21-({(2E,6S)-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}oxy)-16-hydroxy-28-oxoolean-12-en-28-yl]-β-D-glucopyranose

IUPAC Name

β-D-xylopyranosyl-(1→4)-6-deoxy-α-D-mannopyranosyl-(1→2)-1-O-[(3β,16α,21β)-3-{[α-L-arabinopyranosyl-(1→2)-6-deoxy-β-D-galactopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl]oxy}-21-({(2E,6S)-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}oxy)-16-hydroxy-28-oxoolean-12-en-28-yl]-β-D-glucopyranose

Registry Numbers	Sources
Reaxys:11058834	Reaxys

Citations