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 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
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Registry Number Type Source
155-58-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
12 August 2021