ContaminantDB: Arbutin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:26:11 UTC

Update Date

2016-11-09 01:15:36 UTC

Accession Number

CHEM017529

Identification

Common Name

Arbutin

Class

Small Molecule

Description

A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Hydroquinone-O-beta-D-glucopyranoside	ChEBI
p-Hydroxyphenyl beta-D-glucopyranoside	ChEBI
p-Hydroxyphenyl beta-D-glucoside	ChEBI
Ursin	ChEBI
Uvasol	ChEBI
Hydroquinone-O-b-D-glucopyranoside	Generator
Hydroquinone-O-β-D-glucopyranoside	Generator
p-Hydroxyphenyl b-D-glucopyranoside	Generator
p-Hydroxyphenyl β-D-glucopyranoside	Generator
p-Hydroxyphenyl b-D-glucoside	Generator
p-Hydroxyphenyl β-D-glucoside	Generator
4-Hydroxyphenyl-b-glucopyranoside	HMDB
4-Hydroxyphenyl-β-glucopyranoside	HMDB
4-Hydroxyphenyl beta-D-glucopyranoside	HMDB
4-Hydroxyphenyl β-D-glucopyranoside	HMDB
Arbutine	HMDB
Arbutoside	HMDB
Arbutyne	HMDB
Hydroquinone beta-D-glucopyranoside	HMDB
Hydroquinone glucose	HMDB
Hydroquinone β-D-glucopyranoside	HMDB
beta-Arbutin	HMDB
p-Arbutin	HMDB
Β-arbutin	HMDB
Arbutin	ChEBI

Chemical Formula

C₁₂H₁₆O₇

Average Molecular Mass

272.251 g/mol

Monoisotopic Mass

272.090 g/mol

CAS Registry Number

497-76-7

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

Traditional Name

β-arbutin

SMILES

[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

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

InChI Key

BJRNKVDFDLYUGJ-RMPHRYRLSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:18305 )
monosaccharide derivative (CHEBI:18305 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	39.1 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.9	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.16 m³·mol⁻¹	ChemAxon
Polarizability	25.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0uxr-1971000000-e8260464bad4d4a7fa0c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxs-0940000000-9984522469f86670798f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0r00-9750000000-b52a5d3b5fb7e98f0009	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0002-0090000000-a7028a3a9618849334b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0229-0920000000-532b692f9942a62cc7c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0229-0910000000-1cb0580496288b7004fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0950000000-4bafd0325d0163331c0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0950000000-ffffdfe1cd448f0ea135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-016r-0290000000-0ebc801fded534434aa5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-016r-0390000000-5831b5a141106482d24d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4i-0900000000-e517344bdabb66a133e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a4i-0900000000-315daa57d6f694ca71fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a4i-1900000000-df811a65eba1be7fd68d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-0900000000-4efe3ed1e7614387deb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-9000000000-6f8b05f1e0b20e00a25f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-9100000000-7092290163d035871936	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0900000000-a0b2ea306ed135900292	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0a4i-1900000000-26385cb99dd5b38d4f3c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-0900000000-0a4c12f1e9730c4685ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0970000000-e87519bd2c30ca193e5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-f812a22889a4e7871758	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-9600000000-9a8f2b8fb568a07413b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-1890000000-cb67c77a9f0c57c986bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1910000000-52b74ad8f6f3181df26d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-45bf1851196d0254c239	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-0950000000-597b2277ebb9d13fbb41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-4940000000-6a46c2768079c1935cb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-56f28af9a02294ffb2fa	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum