CHEBI:6988 - monotropein

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name monotropein
ChEBI ID CHEBI:6988
Definition An 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C16H22O11
Net Charge 0
Average Mass 390.33930
Monoisotopic Mass 390.11621
InChI InChI=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
InChIKey HPWWQPXTUDMRBI-NJPMDSMTSA-N
SMILES [H][C@]12C=C[C@](O)(CO)[C@@]1([H])[C@@H](OC=C2C(O)=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing monotropein (CHEBI:6988) has role anti-inflammatory agent (CHEBI:67079)
monotropein (CHEBI:6988) has role metabolite (CHEBI:25212)
monotropein (CHEBI:6988) is a β-D-glucoside (CHEBI:22798)
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)
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
Monotropeine ChemIDplus
Manual Xrefs Databases
C00003089 KNApSAcK
C09788 KEGG COMPOUND
CN101817856 Patent
LMPR0102070012 LIPID MAPS
View more database links
Registry Numbers Types Sources
5945-50-6 CAS Registry Number KEGG COMPOUND
5945-50-6 CAS Registry Number ChemIDplus
60559 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16204945 PubMed citation Europe PMC
23261679 PubMed citation Europe PMC
Last Modified
28 July 2014