CHEBI:8824 - trans-rhaponticin

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ChEBI Name trans-rhaponticin
ChEBI ID CHEBI:8824
ChEBI ASCII Name trans-rhaponticin
Definition A rhaponticin in which the double bond adopts a trans-configuration. It possesses a range of pharmacological activities including antitumour, antiinflammatory, antilipemic and neuroprotective activities.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H24O9
Net Charge 0
Average Mass 420.414
Monoisotopic Mass 420.14203
InChI InChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1
InChIKey GKAJCVFOJGXVIA-DXKBKAGUSA-N
SMILES COC1=CC=C(\C=C\C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1O
Metabolite of Species Details
Rheum palmatum (NCBI:txid137221) Found in rhizome (BTO:0001181). See: PubMed
Rheum tanguticum (NCBI:txid137226) See: DOI
Rheum undulatum (NCBI:txid137227) See: PubMed
Vitis vinifera (NCBI:txid29760) Found in leaf (BTO:0000713). See: PubMed
Rheum rhabarbarum (NCBI:txid3621) Found in root (BTO:0001188). See: DOI
Rheum rhaponticum (NCBI:txid46087) See: DOI
Trigonella foenum-graecum (NCBI:txid78534) Found in seed (BTO:0001226). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 2.3.1.85 (fatty acid synthase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of fatty acid synthase (EC 2.3.1.85), a multi-enzyme protein involved in fatty acid synthesis.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
hypoglycemic agent
A drug which lowers the blood glucose level.
anti-allergic agent
A drug used to treat allergic reactions.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
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ChEBI Ontology
Outgoing trans-rhaponticin (CHEBI:8824) has functional parent rhapontigenin (CHEBI:174376)
trans-rhaponticin (CHEBI:8824) has role angiogenesis inhibitor (CHEBI:48422)
trans-rhaponticin (CHEBI:8824) has role anti-allergic agent (CHEBI:50857)
trans-rhaponticin (CHEBI:8824) has role anti-inflammatory agent (CHEBI:67079)
trans-rhaponticin (CHEBI:8824) has role antilipemic drug (CHEBI:35679)
trans-rhaponticin (CHEBI:8824) has role antineoplastic agent (CHEBI:35610)
trans-rhaponticin (CHEBI:8824) has role apoptosis inducer (CHEBI:68495)
trans-rhaponticin (CHEBI:8824) has role EC 2.3.1.85 (fatty acid synthase) inhibitor (CHEBI:71476)
trans-rhaponticin (CHEBI:8824) has role hypoglycemic agent (CHEBI:35526)
trans-rhaponticin (CHEBI:8824) has role neuroprotective agent (CHEBI:63726)
trans-rhaponticin (CHEBI:8824) has role plant metabolite (CHEBI:76924)
trans-rhaponticin (CHEBI:8824) is a rhaponticin (CHEBI:92176)
Incoming 6-O-malonyl-trans-rhaponticin (CHEBI:177370) has functional parent trans-rhaponticin (CHEBI:8824)
IUPAC Name
3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl β-D-glucopyranoside
Synonyms Sources
(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol IUPAC
(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol IUPAC
(E)-rhaponticin ChEBI
ponticin ChemIDplus
rhaponticin ChemIDplus
rhaponticin UniProt
rhaponticine ChemIDplus
rhapontin ChemIDplus
Manual Xrefs Databases
C00002904 KNApSAcK
C10288 KEGG COMPOUND
FDB008525 FooDB
LMPK13090002 LIPID MAPS
Rhaponticin Wikipedia
View more database links
Registry Number Type Source
155-58-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
11 October 2024