CHEBI:18305 - hydroquinone O-β-D-glucopyranoside

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ChEBI Name hydroquinone O-β-D-glucopyranoside
ChEBI ID CHEBI:18305
ChEBI ASCII Name hydroquinone O-beta-D-glucopyranoside
Definition A monosaccharide derivative that is hydroquinone attached to a β-D-glucopyranosyl residue at position 4 via a glycosidic linkage.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2806, CHEBI:14417
Supplier Information ChemicalBook:CB6670456, eMolecules:478502, Selleckchem:Arbutin(Uva,-p-Arbutin), ZINC000000518554
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β-Arbutin, also known by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar stereoisomer, α-arbutin, which exhibits similar effects in clinical applications.
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Formula C12H16O7
Net Charge 0
Average Mass 272.25120
Monoisotopic Mass 272.08960
InChI InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
InChIKey BJRNKVDFDLYUGJ-RMPHRYRLSA-N
SMILES OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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 hydroquinone O-β-D-glucopyranoside (CHEBI:18305) has functional parent hydroquinone (CHEBI:17594)
hydroquinone O-β-D-glucopyranoside (CHEBI:18305) has role Escherichia coli metabolite (CHEBI:76971)
hydroquinone O-β-D-glucopyranoside (CHEBI:18305) has role plant metabolite (CHEBI:76924)
hydroquinone O-β-D-glucopyranoside (CHEBI:18305) is a β-D-glucoside (CHEBI:22798)
hydroquinone O-β-D-glucopyranoside (CHEBI:18305) is a monosaccharide derivative (CHEBI:63367)
Incoming arbutin 6-phosphate (CHEBI:2807) has functional parent hydroquinone O-β-D-glucopyranoside (CHEBI:18305)
hyemaloside A (CHEBI:66051) has functional parent hydroquinone O-β-D-glucopyranoside (CHEBI:18305)
hyemaloside C (CHEBI:66052) has functional parent hydroquinone O-β-D-glucopyranoside (CHEBI:18305)
IUPAC Name
4-hydroxyphenyl β-D-glucopyranoside
Synonyms Sources
Arbutin KEGG COMPOUND
hydroquinone O-β-D-glucopyranoside UniProt
Hydroquinone-O-beta-D-glucopyranoside KEGG COMPOUND
p-hydroxyphenyl β-D-glucopyranoside ChemIDplus
p-hydroxyphenyl β-D-glucoside ChemIDplus
Ursin KEGG COMPOUND
Uvasol KEGG COMPOUND
Manual Xrefs Databases
4267 DrugCentral
Arbutin Wikipedia
C00002638 KNApSAcK
C06186 KEGG COMPOUND
HMDB0029943 HMDB
HYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE MetaCyc
LSM-5255 LINCS
View more database links
Registry Numbers Types Sources
497-76-7 CAS Registry Number KEGG COMPOUND
497-76-7 CAS Registry Number ChemIDplus
89673 Reaxys Registry Number Reaxys
Citations Types Sources
15287073 PubMed citation Europe PMC
9518563 PubMed citation Europe PMC
Last Modified
22 February 2017