ContaminantDB: Dihydrocaffeic acid 3-O-glucuronide

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

Record Information

Version

1.0

Creation Date

2016-05-27 01:34:56 UTC

Update Date

2016-11-09 01:22:30 UTC

Accession Number

CHEM041590

Identification

Common Name

Dihydrocaffeic acid 3-O-glucuronide

Class

Small Molecule

Description

Dihydrocaffeic acid 3-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dihydrocaffeate 3-O-glucuronide	Generator
(2S,3S,4S,5R,6S)-6-[5-(2-Carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₁₅H₁₈O₁₀

Average Molecular Mass

358.297 g/mol

Monoisotopic Mass

358.090 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-[5-(2-carboxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

SMILES

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

InChI Identifier

InChI=1S/C15H18O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1,3,5,10-13,15-16,19-21H,2,4H2,(H,17,18)(H,22,23)/t10-,11-,12+,13-,15+/m0/s1

InChI Key

AELQNMHOLDHBFA-DKBOKBLXSA-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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
3-phenylpropanoic-acid
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Hydroxy acid
Pyran
Oxane
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Monosaccharide
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
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	8.41 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-0.5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.94 m³·mol⁻¹	ChemAxon
Polarizability	32.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btl-9374000000-a527bdcdf4d1675e7a9f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-2022049000-3d0af10c1faceed1e119	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	splash10-00l6-0809000000-6a8e8652e0e3e36d06ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-0901000000-57e423ee4a0042771255	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00y0-1900000000-c6783fb6424348544c65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bu0-1619000000-8b47365776e7d6b12402	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-1912000000-96fb6f85e72f11a587c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06si-4900000000-312a19448c11dead52a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0917000000-75a0fe5ee7267ddf01b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-5932000000-1538cf53f8b164bda5bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1900000000-e24dc88553f51364ddac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-0927000000-7ecf6344c35f65c2bba5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0912000000-bbb8c2179455671bd273	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06di-0900000000-8e2328a75df41eb915b3	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

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

HMDB0041720

FooDB ID

FDB029886

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

30777618

ChEBI ID

Not Available

PubChem Compound ID

49844972

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.

Dihydrocaffeic acid 3-O-glucuronide (CHEM041590)

Structure for CHEM041590: Dihydrocaffeic acid 3-O-glucuronide