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CHEBI:6988 - monotropein

ChEBI IDCHEBI:6988
ChEBI Namemonotropein
Stars
DefinitionAn iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a β-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and hydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer).
Last Modified28 July 2014
DownloadsMolfile
FormulaC16H22O11
Net Charge0
Average Mass390.341
Monoisotopic Mass390.11621
SMILES[H][C@]12[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)O)[C@@]1([H])C=C[C@]2(O)CO
InChIInChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1
InChIKeyHPWWQPXTUDMRBI-NJPMDSMTSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
monotropein (CHEBI:6988) has role anti-inflammatory agent (CHEBI:67079)
monotropein (CHEBI:6988) has role metabolite (CHEBI:25212)
monotropein (CHEBI:6988) is a cyclopentapyran (CHEBI:38606)
monotropein (CHEBI:6988) is a iridoid monoterpenoid (CHEBI:50563)
monotropein (CHEBI:6988) is a monocarboxylic acid (CHEBI:25384)
monotropein (CHEBI:6988) is a monosaccharide derivative (CHEBI:63367)
monotropein (CHEBI:6988) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(1S,4aS,7R,7aS)-1-(β-D-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
Synonym  Source
MonotropeineChemIDplus
Manual XrefsDatabases
C09788KEGG COMPOUND
LMPR0102070012LIPID MAPS
CN101817856Patent
C00003089KNApSAcK
Registry NumbersSources
Reaxys:60559Reaxys
CAS:5945-50-6KEGG COMPOUND
CAS:5945-50-6ChemIDplus
Citations