ContaminantDB: 2-O-Caffeoylarbutin

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

Record Information

Version

1.0

Creation Date

2016-05-25 22:15:10 UTC

Update Date

2016-11-09 01:18:02 UTC

Accession Number

CHEM025234

Identification

Common Name

2-O-Caffeoylarbutin

Class

Small Molecule

Description

2-O-Caffeoylarbutin is found in fruits. 2-O-Caffeoylarbutin is isolated from leaves of Vaccinium vitis-idaea (mountain cranberry

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,5-Dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	HMDB

Chemical Formula

C₂₁H₂₂O₁₀

Average Molecular Mass

434.393 g/mol

Monoisotopic Mass

434.121 g/mol

CAS Registry Number

230955-36-9

IUPAC Name

4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

SMILES

OCC1OC(OC2=CC=C(O)C=C2)C(OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)C1O

InChI Identifier

InChI=1S/C21H22O10/c22-10-16-18(27)19(28)20(21(30-16)29-13-5-3-12(23)4-6-13)31-17(26)8-2-11-1-7-14(24)15(25)9-11/h1-9,16,18-25,27-28H,10H2/b8-2+

InChI Key

SAHZOJQMDIDFST-KRXBUXKQSA-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
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Catechol
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Oxane
Fatty acyl
Monosaccharide
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.69 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.52	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.69 m³·mol⁻¹	ChemAxon
Polarizability	42.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-022i-7942200000-477cc91bdcceff601ea8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-000i-3921116000-41672bdb24fd5eccd19e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0920300000-14be6f4ef537e487a443	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0910000000-dc7c6c189c55dd97c36f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-53ac8f12a98cd6ce4432	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0560-0930400000-23d0b2a081f8f6a0c9fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0910000000-4ac1b0ce503a7c63de2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1900000000-7a00bceb20a1d537c30e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0109000000-a2b54c12f1a9d648f831	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08g1-0904100000-528315dd988f2c054b4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rj-3910000000-8aa814ab7aef77fd8b7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-0614900000-48081fabe2e08372332b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1924000000-ea36bd5516fffebb334a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-5902000000-3515ac52457fdb090df8	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031347

FooDB ID

FDB003411

Phenol Explorer ID

Not Available

KNApSAcK ID

C00054559

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

131751154

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

2-O-Caffeoylarbutin (CHEM025234)

Structure for CHEM025234: 2-O-Caffeoylarbutin