CHEBI:65424 - 3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A
ChEBI ID CHEBI:65424
ChEBI ASCII Name 3beta-O-{alpha-L-Rhap-(1->2)-beta-D-Glcp-(1->4)-[beta-D-Glcp-(1->2)]-alpha-L-Arap}primulagenin A
Definition A triterpenoid saponin that is composed of primulagenin A having a α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl moiety attached to position 3 by a glycosidic linkage. It is isolated from the whole plants of Ardisia pusilla and exhibits cytotoxic activity against human gliboblastoma U251MG cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C53H88O21
Net Charge 0
Average Mass 1061.25320
Monoisotopic Mass 1060.58181
InChI InChI=1S/C53H88O21/c1-23-33(58)37(62)40(65)44(68-23)74-43-39(64)35(60)27(20-55)70-47(43)71-28-21-67-46(42(36(28)61)73-45-41(66)38(63)34(59)26(19-54)69-45)72-32-12-13-50(6)29(49(32,4)5)11-14-51(7)30(50)10-9-24-25-17-48(2,3)15-16-53(25,22-56)31(57)18-52(24,51)8/h9,23,25-47,54-66H,10-22H2,1-8H3/t23-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37+,38-,39-,40+,41+,42+,43+,44-,45-,46-,47-,50-,51+,52+,53+/m0/s1
InChIKey KNJZSRUBTKLEDR-FXRKFYLMSA-N
SMILES [H][C@@]1(CO[C@@]([H])(O[C@H]2CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC=C3[C@]5([H])CC(C)(C)CC[C@]5(CO)[C@H](O)C[C@@]43C)C2(C)C)[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@]1([H])O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
Metabolite of Species Details
Lysimachia clethroides (NCBI:txid167892) Found in aerial part (BTO:0001658). Air-dried, powdered aerial parts were extracted with 70% aqueous ethyl alcohol. See: PubMed
Ardisia pusilla (NCBI:txid587403) 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 3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) has functional parent primulagenin A (CHEBI:70978)
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) has role antineoplastic agent (CHEBI:35610)
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) has role plant metabolite (CHEBI:76924)
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) is a pentacyclic triterpenoid (CHEBI:25872)
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) is a tetrasaccharide derivative (CHEBI:63567)
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α)-16,28-dihydroxyolean-12-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside
Synonyms Sources
3β-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-16α,28-dihydroxy-olean-12-ene ChEBI
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}-16α,28-dihydroxyolean-12-ene ChEBI
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}-primulagenin A ChEBI
Ardisia saponin ChEBI
Registry Number Type Source
22007805 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19039733 PubMed citation Europe PMC
21928797 PubMed citation Europe PMC
Last Modified
20 January 2014