CHEBI:8113 - phlorizin

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ChEBI Name phlorizin
ChEBI ID CHEBI:8113
Definition An aryl β-D-glucoside that is phloretin attached to a β-D-glucopyranosyl residue at position 2' via a glycosidic linkage.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5159244, eMolecules:474218
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Lenalidomide, sold under the brand name Revlimid among others, is a medication used to treat multiple myeloma, smoldering myeloma, and myelodysplastic syndromes (MDS). For multiple myeloma, it is a first line treatment, and is given with dexamethasone. It is taken by mouth. Common side effects include diarrhea, itchiness, joint pain, fever, headache, and trouble sleeping. Severe side effects include low blood platelets, low white blood cells, and blood clots. The dose may need to be adjusted in people with kidney problems. Lenalidomide is closely related to thalidomide, which is known to cause severe birth defects, so its use during pregnancy is very likely to harm the fetus. Lenalidomide belongs to a class of drugs known as immunomodulatory imide drugs (IMiDs) or Cereblon E3 ligase modulators, which includes thalidomide and its analogs. In lymphocytes, these drugs target an E3 ubiquitin ligase and change its specificity to include new targets. This results in the rapid degradation of several disease-related proteins including IKZF1, IKZF3, and CSNK1A1. Lenalidomide was approved for medical use in the United States in 2005. It is on the World Health Organization's List of Essential Medicines.
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Formula C21H24O10
Net Charge 0
Average Mass 436.40926
Monoisotopic Mass 436.13695
InChI InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChIKey IOUVKUPGCMBWBT-QNDFHXLGSA-N
SMILES OC[C@H]1O[C@@H](Oc2cc(O)cc(O)c2C(=O)CCc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
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ChEBI Ontology
Outgoing phlorizin (CHEBI:8113) has functional parent phloretin (CHEBI:17276)
phlorizin (CHEBI:8113) has role antioxidant (CHEBI:22586)
phlorizin (CHEBI:8113) has role plant metabolite (CHEBI:76924)
phlorizin (CHEBI:8113) is a aryl β-D-glucoside (CHEBI:28749)
phlorizin (CHEBI:8113) is a dihydrochalcones (CHEBI:71230)
phlorizin (CHEBI:8113) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name
3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside
Synonyms Sources
Floridzin ChemIDplus
Phloretin 2'-glucoside ChemIDplus
Phlorhizin KEGG COMPOUND
Phloridzin KEGG COMPOUND
phlorizin UniProt
Phlorizin KEGG COMPOUND
Phlorizoside ChemIDplus
Manual Xrefs Databases
C00000990 KNApSAcK
C01604 KEGG COMPOUND
CN102697895 Patent
CN103214530 Patent
CPD-12447 MetaCyc
HMDB0036634 HMDB
LSM-25654 LINCS
Phlorizin Wikipedia
View more database links
Registry Numbers Types Sources
60-81-1 CAS Registry Number ChemIDplus
66621 Reaxys Registry Number Reaxys
Citations Types Sources
18573104 PubMed citation Europe PMC
24392851 PubMed citation Europe PMC
Last Modified
06 January 2017