albizoside A (CHEBI:65379)

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CHEBI:65379 - albizoside A

ChEBI ID	CHEBI:65379
ChEBI Name	albizoside A
Stars
Definition	A triterpenoid saponin isolated from the stem bark of Albizia chinensis that exhibits cytotoxic activity against a small panel of human tumour cell lines.
Last Modified	16 January 2014
Downloads	Molfile

Formula	C118H186O56
Net Charge	0
Average Mass	2500.730
Monoisotopic Mass	2499.17067
SMILES	[H][C@@]1(O[C@H]2[C@@H](O)[C@]([H])(O[C@H]3[C@H](OC(=O)[C@]45C[C@]([H])(OC(=O)/C(=C/CC[C@@](C)(C=C)O[C@]6([H])O[C@H](C)[C@@H](OC(=O)/C(C)=C/CC[C@@](C)(C=C)O[C@@H]7O[C@H](C)[C@@H](O)[C@H](O)[C@H]7OC(=O)/C(=C/CC[C@@](C)(C=C)O[C@@H]7O[C@H](C)[C@@H](O)[C@H](O)[C@H]7O)CO)[C@H](O)[C@H]6O)CO)C(C)(C)C[C@@]4([H])C4=CC[C@]6([H])[C@@]7(C)CC[C@H](O[C@]8([H])O[C@H](CO[C@@H]9O[C@H](C)[C@H](O)[C@H](O)[C@H]9O[C@]9([H])OC[C@@H](O)[C@H](O)[C@H]9O)[C@@H](O)[C@H](O)[C@H]8O)C(C)(C)[C@]7([H])CC[C@@]6(C)[C@]4(C)C[C@H]5O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@@H](C)[C@]2([H])O[C@@H]2O[C@@H](CO)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C118H186O56/c1-20-112(14,172-104-87(145)76(134)68(126)49(5)154-104)35-25-28-55(42-120)98(150)166-95-80(138)70(128)51(7)156-108(95)174-114(16,22-3)33-23-26-48(4)96(148)165-90-52(8)158-105(88(146)82(90)140)173-113(15,21-2)34-24-27-54(41-119)97(149)163-67-40-118(109(151)171-107-94(81(139)73(131)60(44-122)161-107)170-103-89(147)92(168-102-86(144)77(135)72(130)59(43-121)159-102)91(53(9)157-103)167-101-84(142)74(132)61(45-123)160-101)57(38-110(67,10)11)56-29-30-64-115(17)36-32-66(111(12,13)63(115)31-37-116(64,18)117(56,19)39-65(118)125)164-100-85(143)78(136)75(133)62(162-100)47-153-106-93(79(137)69(127)50(6)155-106)169-99-83(141)71(129)58(124)46-152-99/h20-22,26-29,49-53,57-95,99-108,119-147H,1-3,23-25,30-47H2,4-19H3/b48-26+,54-27+,55-28+/t49-,50-,51-,52-,53+,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+,92+,93-,94-,95-,99+,100+,101+,102+,103+,104+,105+,106-,107+,108+,112-,113-,114-,115+,116-,117-,118-/m1/s1
InChIKey	HURMKHBJYJPKHH-UTEFUEFASA-N

Species of Metabolite	Component	Source	Comments
Albizia chinensis (IPNI:473204-1)	stem (BTO:0001300)	PubMed (19256478)	Previous component: stem bark;

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)
	albizoside A (CHEBI:65379) has functional parent acacic acid (CHEBI:70803)
	albizoside A (CHEBI:65379) has role antineoplastic agent (CHEBI:35610)
	albizoside A (CHEBI:65379) has role plant metabolite (CHEBI:76924)
	albizoside A (CHEBI:65379) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
α-L-arabinofuranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-6-deoxy-α-L-mannopyranosyl-(1→2)-1-O-[(3β,16α,21β)-21-{[(2E,6S)-6-({6-deoxy-4-O-[(2E,6S)-6-({6-deoxy-2-O-[(2E,6S)-6-[(6-deoxy-β-D-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]-β-D-glucopyranosyl}oxy)-2,6-dimethylocta-2,7-dienoyl]-β-D-glucopyranosyl}oxy)-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxy}-16-hydroxy-28-oxo-3-{[β-D-xylopyranosyl-(1→2)-6-deoxy-β-D-galactopyranosyl-(1→6)-β-D-glucopyranosyl]oxy}olean-12-en-28-yl]-β-D-glucopyranose

IUPAC Name

α-L-arabinofuranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-6-deoxy-α-L-mannopyranosyl-(1→2)-1-O-[(3β,16α,21β)-21-{[(2E,6S)-6-({6-deoxy-4-O-[(2E,6S)-6-({6-deoxy-2-O-[(2E,6S)-6-[(6-deoxy-β-D-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]-β-D-glucopyranosyl}oxy)-2,6-dimethylocta-2,7-dienoyl]-β-D-glucopyranosyl}oxy)-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxy}-16-hydroxy-28-oxo-3-{[β-D-xylopyranosyl-(1→2)-6-deoxy-β-D-galactopyranosyl-(1→6)-β-D-glucopyranosyl]oxy}olean-12-en-28-yl]-β-D-glucopyranose

Synonym	Source
21-O-{(2E,6S)-2-hydroxymethyl-6-methyl-6-O-{4-O-(2'E,6'S)-2',6'-dimethyl-6'-O-[2'-O-(2''E,6''S)-2''-hydroxymethyl-6''-methyl-6''-O-β-D-quinovopyranosyl-2'',7''-octadienoyl-β-D-quinovopyranosyl]-2',7'-octadienoyl-β-D-quinovopyranosyl}-2,7-octadienoyl}-3-O-[β-D-xylopyranosyl-(1→2)-β-D-fucopyranosyl-(1→6)-β-D-glucopyranosyl]acacic acid 28-O-β-D-glucopyranosyl-(1→3)-[α-L-arabinofuranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester	ChEBI

Synonym

Source

21-O-{(2E,6S)-2-hydroxymethyl-6-methyl-6-O-{4-O-(2'E,6'S)-2',6'-dimethyl-6'-O-[2'-O-(2''E,6''S)-2''-hydroxymethyl-6''-methyl-6''-O-β-D-quinovopyranosyl-2'',7''-octadienoyl-β-D-quinovopyranosyl]-2',7'-octadienoyl-β-D-quinovopyranosyl}-2,7-octadienoyl}-3-O-[β-D-xylopyranosyl-(1→2)-β-D-fucopyranosyl-(1→6)-β-D-glucopyranosyl]acacic acid 28-O-β-D-glucopyranosyl-(1→3)-[α-L-arabinofuranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester

ChEBI

Registry Numbers	Sources
Reaxys:19854331	Reaxys

Citations