ContaminantDB: Taraxinic acid glucosyl ester

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

Record Information

Version

1.0

Creation Date

2016-05-26 00:58:40 UTC

Update Date

2016-11-09 01:18:50 UTC

Accession Number

CHEM029166

Identification

Common Name

Taraxinic acid glucosyl ester

Class

Small Molecule

Description

Taraxinic acid glucosyl ester is found in alcoholic beverages. Taraxinic acid glucosyl ester is a constituent of Taraxacum officinale (dandelion).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Taraxinate glucosyl ester	Generator
(-)-Taraxinic acid beta-glucopyranosyl ester	HMDB
Taraxinic acid beta-glucopyranosyl ester	HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₈O₉

Average Molecular Mass

424.442 g/mol

Monoisotopic Mass

424.173 g/mol

CAS Registry Number

75911-14-7

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

SMILES

C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H28O9/c1-10-4-3-5-12(6-7-13-11(2)19(26)28-14(13)8-10)20(27)30-21-18(25)17(24)16(23)15(9-22)29-21/h5,8,13-18,21-25H,2-4,6-7,9H2,1H3/b10-8-,12-5+

InChI Key

SIOXYUXOHTZOOM-INAGUISBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Terpene glycoside
Germacrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.84 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	0.97	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.09 m³·mol⁻¹	ChemAxon
Polarizability	43.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-0a4i-9314200000-f036712834a8ce29cc0b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-004i-3394038000-ac22015b2e50b547b4cc	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0490300000-afa79b42ed7e008d26b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-0790000000-9ddd12e7cf4e5e3f8737	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-3950000000-a98741cd15ab763157b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-1291400000-bdf07daabf1f44a5c1e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-2390100000-428eb5620eceb76a57e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0903-7390000000-f4d6cac15200159ff2b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0151900000-858a5a4e7e9b4083f7ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-2291100000-b7aea0c2729f6b680d43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016s-6491000000-85578ec0da06d4e88912	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0422900000-23318915ba361ee2f6d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0w90-6339200000-f60b6b9b3d77a48d7e82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-6490100000-a9d6135474914c39dc79	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum