avenacoside A (CHEBI:2937)

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CHEBI:2937 - avenacoside A

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ChEBI ID	CHEBI:2937
ChEBI Name	avenacoside A
Stars
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 into 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.
Last Modified	28 April 2020
Downloads	Molfile

Formula	C51H82O23
Net Charge	0
Average Mass	1063.194
Monoisotopic Mass	1062.52469
SMILES	[H][C@@]12CC=C3C[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]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])C[C@]2([H])O[C@]3(CC[C@@](C)(CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)O3)[C@@H](C)[C@]12[H]
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

Roles Classification

Biological Roles:

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

ChEBI Ontology

Outgoing Relation(s)
	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 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)
	avenacoside A (CHEBI:2937) is a β-D-glucoside (CHEBI:22798)
Incoming Relation(s)
	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

Synonym	Source
nuatigenin 3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside}-26-O-β-D-glucopyranoside	ChEBI

UniProt Name	Source
avenacoside A	UniProt

Manual Xrefs	Databases
C08887	KEGG COMPOUND
HMDB0033815	HMDB
C00003564	KNApSAcK

Registry Numbers	Sources
Reaxys:22997420	Reaxys

Citations