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CHEBI:69247 - meso-3,3'-didemethoxynectandrin B

ChEBI IDCHEBI:69247
ChEBI Namemeso-3,3'-didemethoxynectandrin B
Stars
ASCII Namemeso-3,3'-didemethoxynectandrin B
DefinitionA lignan that consists of a 3,4-dimethyloxolane ring substituted by 4-hydroxyphenyl groups at positions 2 and 5 respectively (the 2R,3R,4S,5S-stereoisomer). Isolated from the roots of Krameria lappacea, it exhibits anti-inflammatory activity.
Last Modified13 April 2015
DownloadsMolfile
FormulaC18H20O3
Net Charge0
Average Mass284.355
Monoisotopic Mass284.14124
SMILESC[C@@H]1[C@H](C)[C@@H](c2ccc(O)cc2)O[C@H]1c1ccc(O)cc1
InChIInChI=1S/C18H20O3/c1-11-12(2)18(14-5-9-16(20)10-6-14)21-17(11)13-3-7-15(19)8-4-13/h3-12,17-20H,1-2H3/t11-,12+,17-,18+
InChIKeyPIBJADPEZQHMQS-FRVJLOGJSA-N
Species of MetaboliteComponentSourceComments
Krameria lappacea (ncbitaxon:228636) root (BTO:0001188) PubMed (21800856) Methylene dichloride extract of dried and ground roots
Roles Classification
Biological Roles:
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) has role anti-inflammatory agent (CHEBI:67079)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) has role NF-κB inhibitor (CHEBI:73240)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) has role plant metabolite (CHEBI:76924)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) is a lignan (CHEBI:25036)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) is a oxolanes (CHEBI:26912)
meso-3,3'-didemethoxynectandrin B (CHEBI:69247) is a phenols (CHEBI:33853)
IUPAC Name 
4,4'-[(2R,3R,4S,5S)-3,4-dimethyloxolane-2,5-diyl]diphenol
Synonym  Source
4-epilarreatricinChEBI
Registry NumbersSources
Reaxys:4236153Reaxys
Citations