CHEBI:2515 - agnuside

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ChEBI Name agnuside
ChEBI ID CHEBI:2515
Definition A benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H26O11
Net Charge 0
Average Mass 466.439
Monoisotopic Mass 466.14751
InChI InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15+,16+,17+,18-,19+,21-,22-/m0/s1
InChIKey GLACGTLACKLUJX-QNAXTHAFSA-N
SMILES [H][C@@]12C=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1([H])C(COC(=O)C1=CC=C(O)C=C1)=C[C@H]2O
Metabolite of Species Details
Scrophularia deserti (NCBI:txid1042505) See: PubMed
Vitex peduncularis (NCBI:txid1489957) Found in bark (BTO:0001301). Isolated from stem bark. See: PubMed
Vitex negundo (NCBI:txid361442) Found in leaf (BTO:0000713). See: PubMed
Vitex agnus-castus (NCBI:txid54477) See: PubMed
Vitex agnus-castus (NCBI:txid54477) Found in fruit (BTO:0000486). See: PubMed
Odontites luteus (NCBI:txid691781) 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.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
pro-angiogenic agent
Any compound that promotes the growth of new blood vessels from pre-existing vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing agnuside (CHEBI:2515) has functional parent aucubin (CHEBI:69796)
agnuside (CHEBI:2515) has role anti-inflammatory agent (CHEBI:67079)
agnuside (CHEBI:2515) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
agnuside (CHEBI:2515) has role plant metabolite (CHEBI:76924)
agnuside (CHEBI:2515) has role pro-angiogenic agent (CHEBI:72571)
agnuside (CHEBI:2515) is a β-D-glucoside (CHEBI:22798)
agnuside (CHEBI:2515) is a benzoate ester (CHEBI:36054)
agnuside (CHEBI:2515) is a cyclopentapyran (CHEBI:38606)
agnuside (CHEBI:2515) is a iridoid monoterpenoid (CHEBI:50563)
agnuside (CHEBI:2515) is a monosaccharide derivative (CHEBI:63367)
agnuside (CHEBI:2515) is a phenols (CHEBI:33853)
agnuside (CHEBI:2515) is a terpene glycoside (CHEBI:61777)
IUPAC Name
[(1S,4aR,5S,7aS)-1-(β-D-glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
Synonyms Sources
(−)-buddlejoside A ChemIDplus
agnoside ChemIDplus
buddlejoside A ChemIDplus
Manual Xrefs Databases
Agnuside Wikipedia
C00003068 KNApSAcK
C09765 KEGG COMPOUND
FDB015465 FooDB
HMDB0036561 HMDB
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Registry Number Type Source
11027-63-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11842334 PubMed citation Europe PMC
13651032 PubMed citation Europe PMC
16797620 PubMed citation Europe PMC
22228102 PubMed citation Europe PMC
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23954198 PubMed citation Europe PMC
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27997755 PubMed citation Europe PMC
29403861 PubMed citation Europe PMC
30183186 PubMed citation Europe PMC
30340142 PubMed citation Europe PMC
31155557 PubMed citation Europe PMC
IND606954418 Agricola citation Europe PMC
Last Modified
01 October 2020