CHEBI:2937 - avenacoside A

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ChEBI Name avenacoside A
ChEBI ID CHEBI:2937
Definition A steroid saponin obtained from grain and leaves of oats (Avena sativa) that is nuatigenin in which the hydroxy group at position 26 is converted to its β-D-glucoside and in which the hydroxy group at position 3 is converted into its methyl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside derivative.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C51H82O23
Net Charge 0
Average Mass 1063.18300
Monoisotopic Mass 1062.52469
InChI InChI=1S/C51H82O23/c1-20-31-27(73-51(20)13-12-48(3,74-51)19-65-44-38(61)36(59)33(56)28(16-52)68-44)15-26-24-7-6-22-14-23(8-10-49(22,4)25(24)9-11-50(26,31)5)67-47-43(72-45-39(62)35(58)32(55)21(2)66-45)41(64)42(30(18-54)70-47)71-46-40(63)37(60)34(57)29(17-53)69-46/h6,20-21,23-47,52-64H,7-19H2,1-5H3/t20-,21-,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-/m0/s1
InChIKey XNKSKPFVXMYCKU-QTPGKRPGSA-N
SMILES [H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@](C)(CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O1)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]2O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing avenacoside A (CHEBI:2937) has functional parent nuatigenin (CHEBI:15574)
avenacoside A (CHEBI:2937) has role metabolite (CHEBI:25212)
avenacoside A (CHEBI:2937) is a β-D-glucoside (CHEBI:22798)
avenacoside A (CHEBI:2937) is a hexacyclic triterpenoid (CHEBI:70994)
avenacoside A (CHEBI:2937) is a spiroketal (CHEBI:72600)
avenacoside A (CHEBI:2937) is a steroid saponin (CHEBI:61655)
avenacoside A (CHEBI:2937) is a trisaccharide derivative (CHEBI:63571)
Incoming 26-desglucoavenacoside A (CHEBI:75932) has functional parent avenacoside A (CHEBI:2937)
avenacoside B (CHEBI:2938) has functional parent avenacoside A (CHEBI:2937)
IUPAC Name
(3β,22S,25S)-3-{[6-deoxy-α-L-mannopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranosyl]oxy}-22,25-epoxyfurost-5-en-26-yl β-D-glucopyranoside
Synonyms Sources
avenacoside A UniProt
nuatigenin 3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside}-26-O-β-D-glucopyranoside ChEBI
Manual Xrefs Databases
C00003564 KNApSAcK
C08887 KEGG COMPOUND
HMDB0033815 HMDB
View more database links
Registry Number Type Source
22997420 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11043466 PubMed citation Europe PMC
21240840 PubMed citation Europe PMC
22972708 PubMed citation Europe PMC
IND20378448 Agricola citation Europe PMC
IND20378495 Agricola citation Europe PMC
IND43646188 Agricola citation Europe PMC
Last Modified
04 August 2014
General Comment
2013-06-13 The structure shown is the revised structure as reported by Pecio, L., Jederejek, D., Masullo, M., Piacente, S., Oleszek, W. and Stochmal, A. (2012) Revised structures of avenacosides A and B and a new sulfated saponin from Avena sativa L. Magn. Reson. Chem., 2012, 50, 755-758.