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CHEBI:65684 - (−)-cubebin

ChEBI IDCHEBI:65684
ChEBI Name(−)-cubebin
Stars
ASCII Name(-)-cubebin
DefinitionA lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities.
Last Modified25 March 2015
DownloadsMolfile
FormulaC20H20O6
Net Charge0
Average Mass356.374
Monoisotopic Mass356.12599
SMILES[H][C@]1(Cc2ccc3c(c2)OCO3)CO[C@H](O)[C@]1([H])Cc1ccc2c(c1)OCO2
InChIInChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2/t14-,15+,20-/m0/s1
InChIKeyDIYWRNLYKJKHAM-MDOVXXIYSA-N
Species of MetaboliteComponentSourceComments
Piper nigrum (ncbitaxon:13216) leaf (BTO:0000713) PubMed (15467205) Mixture of alpha and beta isomer
Roles Classification
Biological Roles:
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
histamine antagonist  Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
histamine antagonist  Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
(−)-cubebin (CHEBI:65684) has role analgesic (CHEBI:35480)
(−)-cubebin (CHEBI:65684) has role anti-inflammatory agent (CHEBI:67079)
(−)-cubebin (CHEBI:65684) has role antimicrobial agent (CHEBI:33281)
(−)-cubebin (CHEBI:65684) has role histamine antagonist (CHEBI:37956)
(−)-cubebin (CHEBI:65684) has role plant metabolite (CHEBI:76924)
(−)-cubebin (CHEBI:65684) has role trypanocidal drug (CHEBI:36335)
(−)-cubebin (CHEBI:65684) is a benzodioxoles (CHEBI:38298)
(−)-cubebin (CHEBI:65684) is a cyclic acetal (CHEBI:59770)
(−)-cubebin (CHEBI:65684) is a lactol (CHEBI:38131)
(−)-cubebin (CHEBI:65684) is a lignan (CHEBI:25036)
(−)-cubebin (CHEBI:65684) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol
Synonyms  Source
9-Hydroxy-3,4:3',4'-bis(methylenedioxy)-9,9'-epoxylignanHMDB
3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-olHMDB
(8R,8'R,9S)-cubebinChEBI
β-cubebinChEBI
Manual XrefsDatabases
HMDB0030682HMDB
EP2517705Patent
JP2011098968Patent
C10549KEGG COMPOUND
C00002591KNApSAcK
Registry NumbersSources
Reaxys:6489121Reaxys
CAS:18423-69-3KEGG COMPOUND
CAS:18423-69-3ChemIDplus
Citations