CHEBI:65425 - ardisianoside A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ardisianoside A
ChEBI ID CHEBI:65425
Definition A triterpenoid saponin that is composed of (3β,16α)-13,28-epoxyoleanane-3,16-diol having a β-D-Glcp-(1→2)-{β-D-Xylp-(1→2)-{β-D-Glcp-(1→3)-[β-D-Glcp-(1→4)]-β-D-Glcp-(1→3)}-β-D-Glcp-(1→4)}-α-L-Arap moiety attached to position 3 by a glycosidic linkage. It is isolated from whole plants of Ardisia japonica and exhibits significant cytotoxicity against a panel of human cancer cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C70H116O36
Net Charge 0
Average Mass 1533.64840
Monoisotopic Mass 1532.72463
InChI InChI=1S/C70H116O36/c1-64(2)14-15-69-25-94-70(35(69)16-64)13-9-34-66(5)11-10-37(65(3,4)33(66)8-12-67(34,6)68(70,7)17-36(69)77)101-62-55(105-60-50(90)46(86)41(81)29(20-73)97-60)43(83)32(24-93-62)100-63-56(106-57-47(87)38(78)26(76)23-92-57)53(42(82)30(21-74)98-63)103-61-51(91)54(104-59-49(89)45(85)40(80)28(19-72)96-59)52(31(22-75)99-61)102-58-48(88)44(84)39(79)27(18-71)95-58/h26-63,71-91H,8-25H2,1-7H3/t26-,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+,58+,59+,60+,61+,62+,63+,66+,67-,68+,69-,70+/m1/s1
InChIKey YRTDPWGTGFRWCS-NVSDYHLPSA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]45OC[C@@]6(CCC(C)(C)C[C@@]46[H])[C@H](O)C[C@@]35C)[C@@]1(C)CC[C@H](O[C@@H]1OC[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@H]3O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C2(C)C
Metabolite of Species Details
Ardisia japonica (NCBI:txid276775) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
Biological Role(s): 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.
(via saponin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ardisianoside A (CHEBI:65425) has functional parent (3β,16α)-13,28-epoxyoleanane-3,16-diol (CHEBI:70987)
ardisianoside A (CHEBI:65425) has parent hydride oleanane (CHEBI:36481)
ardisianoside A (CHEBI:65425) has role antineoplastic agent (CHEBI:35610)
ardisianoside A (CHEBI:65425) has role plant metabolite (CHEBI:76924)
ardisianoside A (CHEBI:65425) is a bridged compound (CHEBI:35990)
ardisianoside A (CHEBI:65425) is a cyclic ether (CHEBI:37407)
ardisianoside A (CHEBI:65425) is a heptasaccharide derivative (CHEBI:63568)
ardisianoside A (CHEBI:65425) is a hexacyclic triterpenoid (CHEBI:70994)
ardisianoside A (CHEBI:65425) is a secondary alcohol (CHEBI:35681)
ardisianoside A (CHEBI:65425) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranoside
Synonyms Sources
(−)-ardisianoside A ChEBI
3β-O-β-D-Glcp-(1→2)-{β-D-Xylp-(1→2)-{β-D-Glcp-(1→3)-[β-D-Glcp-(1→4)]-β-D-Glcp-(1→3)}-β-D-Glcp-(1→4)}-α-L-Arap-13β,28-epoxy-16α-hydroxyoleanane ChEBI
3β-O-β-D-glucopyranosyl-(1→2)-{β-D-xylopyranosyl-(1→2)-{β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranosyl-(1→3)}-β-D-glucopyranosyl-(1→4)}-α-L-arabinopyranosyl-13β,28-epoxy-16α-hydroxyoleanane ChEBI
Registry Number Type Source
11058761 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17243725 PubMed citation Europe PMC
22940450 PubMed citation Europe PMC
Last Modified
20 January 2014