CHEBI:143821 - nepetaside

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ChEBI Name nepetaside
ChEBI ID CHEBI:143821
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information
Download Molfile XML SDF
Formula C16H26O8
Net Charge 0
Average Mass 346.376
Monoisotopic Mass 346.16277
InChI InChI=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
InChIKey CUIDBUWFCFYEPL-PIFFKTMJSA-N
SMILES C[C@H]1COC([C@@]2([C@@H](C)[C@@H](C[C@]12[H])O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[H])=O
Metabolite of Species Details
Nepeta cataria (NCBI:txid39347) Found in aerial part (BTO:0001658). See: DOI
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nepetaside (CHEBI:143821) has role plant metabolite (CHEBI:76924)
nepetaside (CHEBI:143821) is a β-D-glucoside (CHEBI:22798)
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)
IUPAC Name
(4R,4aR,6R,7R,7aS)-4,7-dimethyl-1-oxooctahydrocyclopenta[c]pyran-6-yl β-D-glucopyranoside
Synonym Source
(−)-nepetaside KNApSAcK
Manual Xrefs Databases
C00010642 KNApSAcK
FDB017377 FooDB
HMDB0038149 HMDB
View more database links
Registry Number Type Source
114076-56-1 CAS Registry Number KNApSAcK
Last Modified
17 August 2023
General Comment
2019-06-03 Relevant article: Xie, S., Uesato, S., Inouye, H., Fukita, T., Murai, F., Tagawa, M. and Shingu, T. (1988) Absolute structure of nepetaside, a new iridoid glucoside from Nepeta cataria. Phytochemistry, 27(2), 469-472.