CHEBI:65534 - 22α-methoxy-3-β-O-{β-D-Xylp(1→3)-[β-D-Glcp-(1→2)]-β-D-Glcp-(1→4)-β-D-Glcp}-furost-3β,26-diol 26-O-β-D-Glcp

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ChEBI Name 22α-methoxy-3-β-O-{β-D-Xylp(1→3)-[β-D-Glcp-(1→2)]-β-D-Glcp-(1→4)-β-D-Glcp}-furost-3β,26-diol 26-O-β-D-Glcp
ChEBI ID CHEBI:65534
ChEBI ASCII Name 22alpha-methoxy-3-beta-O-{beta-D-Xylp(1->3)-[beta-D-Glcp-(1->2)]-beta-D-Glcp-(1->4)-beta-D-Glcp}-furost-3beta,26-diol 26-O-beta-D-Glcp
Definition A steroid saponin that consists of (3β,22R)-22-methoxyfurostan-3,26-diol attached to a β-D-glucopyranosyl residue at position 26 and a β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Brunfelsia grandiflora, it exhibits antileishmanial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C57H96O28
Net Charge 0
Average Mass 1229.35530
Monoisotopic Mass 1228.60881
InChI InChI=1S/C57H96O28/c1-22(20-75-50-44(71)40(67)37(64)31(16-58)78-50)8-13-57(74-5)23(2)35-30(85-57)15-28-26-7-6-24-14-25(9-11-55(24,3)27(26)10-12-56(28,35)4)77-52-46(73)42(69)47(34(19-61)81-52)82-54-49(84-53-45(72)41(68)38(65)32(17-59)79-53)48(39(66)33(18-60)80-54)83-51-43(70)36(63)29(62)21-76-51/h22-54,58-73H,6-21H2,1-5H3/t22?,23-,24?,25-,26+,27-,28-,29+,30-,31+,32+,33+,34+,35-,36-,37+,38+,39+,40-,41-,42+,43+,44+,45+,46+,47+,48-,49+,50+,51-,52+,53-,54-,55-,56-,57+/m0/s1
InChIKey QOKZNLCOQRNCTQ-XFBOQIBUSA-N
SMILES [H][C@]12C[C@@]3([H])[C@]4([H])CCC5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@](CCC(C)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)(OC)O2)O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
Metabolite of Species Details
Brunfelsia grandiflora (NCBI:txid1035550) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
(via 22alpha-methoxy-3-beta-O-{beta-D-Xylp(1->3)-[beta-D-Glcp-(1->2)]-beta-D-Glcp-(1->4)-beta-D-Glcp}-furost-3beta,26-diol 26-O-beta-D-Glcp )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via 22alpha-methoxy-3-beta-O-{beta-D-Xylp(1->3)-[beta-D-Glcp-(1->2)]-beta-D-Glcp-(1->4)-beta-D-Glcp}-furost-3beta,26-diol 26-O-beta-D-Glcp )
(via saponin )
Application(s): antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
(via 22alpha-methoxy-3-beta-O-{beta-D-Xylp(1->3)-[beta-D-Glcp-(1->2)]-beta-D-Glcp-(1->4)-beta-D-Glcp}-furost-3beta,26-diol 26-O-beta-D-Glcp )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 22α-methoxy-3-β-O-{β-D-Xylp(1→3)-[β-D-Glcp-(1→2)]-β-D-Glcp-(1→4)-β-D-Glcp}-furost-3β,26-diol 26-O-β-D-Glcp (CHEBI:65534) has parent hydride furostan (CHEBI:24130)
22α-methoxy-3-β-O-{β-D-Xylp(1→3)-[β-D-Glcp-(1→2)]-β-D-Glcp-(1→4)-β-D-Glcp}-furost-3β,26-diol 26-O-β-D-Glcp (CHEBI:65534) has role antileishmanial agent (CHEBI:70868)
22α-methoxy-3-β-O-{β-D-Xylp(1→3)-[β-D-Glcp-(1→2)]-β-D-Glcp-(1→4)-β-D-Glcp}-furost-3β,26-diol 26-O-β-D-Glcp (CHEBI:65534) has role metabolite (CHEBI:25212)
22α-methoxy-3-β-O-{β-D-Xylp(1→3)-[β-D-Glcp-(1→2)]-β-D-Glcp-(1→4)-β-D-Glcp}-furost-3β,26-diol 26-O-β-D-Glcp (CHEBI:65534) is a steroid saponin (CHEBI:61655)
IUPAC Name
(3β,22R)-26-(β-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside
Synonym Source
26-O-β-D-glucopyranosyl 22α-methoxyfurost-3β,26-diol 3-O-β-D-xylopyranosyl(1→3)-{β-D-glucopyranosyl(1→2)}-β-D-glucopyranosyl(1→4)-β-D-glucopyranoside ChEBI
Citation Waiting for Citations Type Source
18175984 PubMed citation Europe PMC
Last Modified
12 July 2016