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CHEBI:143821 - nepetaside

ChEBI IDCHEBI:143821
ChEBI Namenepetaside
Stars
DefinitionA terpene glycoside that is β-D-glucopyranose in which the hydrogen of the hydroxy group at position 1R is replaced by a (4R,4aR,6R,7R,7aS)-4,7-dimethyl-1-oxooctahydrocyclopenta[c]pyran-6-yl group. It is a plant metabolite isolated from Nepeta cataria.
Last Modified17 August 2023
Submittermwilliams
DownloadsMolfile
FormulaC16H26O8
Net Charge0
Average Mass346.376
Monoisotopic Mass346.16277
SMILES[H][C@]12C[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](C)[C@@]1([H])C(=O)OC[C@@H]2C
InChIInChI=1S/C16H26O8/c1-6-5-22-15(21)11-7(2)9(3-8(6)11)23-16-14(20)13(19)12(18)10(4-17)24-16/h6-14,16-20H,3-5H2,1-2H3/t6-,7-,8+,9+,10+,11+,12+,13-,14+,16+/m0/s1
InChIKeyCUIDBUWFCFYEPL-PIFFKTMJSA-N
Species of MetaboliteComponentSourceComments
Nepeta cataria (ncbitaxon:39347) aerial part (BTO:0001658) DOI (10.1016/0031-9422(88)83122-4)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
nepetaside (CHEBI:143821) has role plant metabolite (CHEBI:76924)
nepetaside (CHEBI:143821) is a iridoid monoterpenoid (CHEBI:50563)
nepetaside (CHEBI:143821) is a organic heterobicyclic compound (CHEBI:27171)
nepetaside (CHEBI:143821) is a terpene glycoside (CHEBI:61777)
nepetaside (CHEBI:143821) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(4R,4aR,6R,7R,7aS)-4,7-dimethyl-1-oxooctahydrocyclopenta[c]pyran-6-yl β-D-glucopyranoside
Synonym  Source
(−)-nepetasideKNApSAcK
Manual XrefsDatabases
C00010642KNApSAcK
FDB017377FooDB
HMDB0038149HMDB
Registry NumbersSources
CAS:114076-56-1KNApSAcK