ContaminantDB: Caffeic 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 01:34:35 UTC

Update Date

2016-11-09 01:22:30 UTC

Accession Number

CHEM041575

Identification

Common Name

Caffeic acid 3-O-glucuronide

Class

Small Molecule

Description

Caffeic 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
Caffeate 3-O-glucuronide	Generator
(2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₁₅H₁₆O₁₀

Average Molecular Mass

356.282 g/mol

Monoisotopic Mass

356.074 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

SMILES

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

InChI Identifier

InChI=1S/C15H16O10/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/h1-5,10-13,15-16,19-21H,(H,17,18)(H,22,23)/b4-2+/t10-,11-,12+,13-,15+/m0/s1

InChI Key

BSOMSDFTZKNUHY-ZYZFHZPYSA-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
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Phenol ether
Styrene
Phenoxy compound
Phenol
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Pyran
Benzenoid
Oxane
Monosaccharide
Hydroxy acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	6.29 g/L	ALOGPS
logP	0.69	ALOGPS
logP	-0.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.95	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	5	ChemAxon
Refractivity	79.03 m³·mol⁻¹	ChemAxon
Polarizability	32.07 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	splash10-052r-9354000000-a1df090612e7ece45584	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00c0-2601149000-7399b5b3aa0cfc21a13a	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	splash10-01q0-0819000000-7f76e3b3d77753808a27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0901000000-dffbcafd6d039934c09a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-1900000000-63b5f2d4b2246aecbe46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bvi-1619000000-d29bc89d06ae25debde3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1912000000-e4798d2f7dba480720a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-2900000000-060c19e93edb734a81dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-0906000000-3d12ab9c402a93454ebd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0911000000-90e3e1c0bb702fd7ece6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-0900000000-f379172c6d69fd66e436	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0819000000-479ec1337f224b453ad5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3921000000-93e51acc03012c33dec0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1910000000-c6e8fb2523ce090502db	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

HMDB0041705

FooDB ID

FDB029870

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

30777604

ChEBI ID

Not Available

PubChem Compound ID

25171992

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.

Caffeic acid 3-O-glucuronide (CHEM041575)

Structure for CHEM041575: Caffeic acid 3-O-glucuronide