CHEBI:65684 - (−)-cubebin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (−)-cubebin
ChEBI ID CHEBI:65684
ChEBI ASCII Name (-)-cubebin
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H20O6
Net Charge 0
Average Mass 356.36920
Monoisotopic Mass 356.126
InChI InChI=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
InChIKey DIYWRNLYKJKHAM-MDOVXXIYSA-N
SMILES [H][C@@]1(CO[C@H](O)[C@]1([H])Cc1ccc2OCOc2c1)Cc1ccc2OCOc2c1
Metabolite of Species Details
Piper nigrum (NCBI:13216) Found in leaf (BTO:0000713). Mixture of alpha and beta isomer See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-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 Sources
(8R,8'R,9S)-cubebin ChEBI
3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol HMDB
9-Hydroxy-3,4:3',4'-bis(methylenedioxy)-9,9'-epoxylignan HMDB
β-cubebin ChEBI
Database Links Databases
C00002591 KNApSAcK
C10549 KEGG COMPOUND
EP2517705 Patent
HMDB30682 HMDB
JP2011098968 Patent
View more database links
Registry Numbers Types Sources
18423-69-3 CAS Registry Number ChemIDplus
6489121 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15467205 PubMed citation Europe PMC
17053932 PubMed citation Europe PMC
17236178 PubMed citation Europe PMC
21385598 PubMed citation Europe PMC
21941916 PubMed citation Europe PMC
Last Modified
25 March 2015