ContaminantDB: Luteic acid

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

Record Information

Version

1.0

Creation Date

2016-05-25 22:51:18 UTC

Update Date

2016-11-09 01:18:13 UTC

Accession Number

CHEM026203

Identification

Common Name

Luteic acid

Class

Small Molecule

Description

Luteic acid, also known as luteate, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Luteic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Luteic acid can be found in guava, which makes luteic acid a potential biomarker for the consumption of this food product. Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin .

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
3,4,8,9,10-Pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylate	Generator
Luteate	Generator

Chemical Formula

C₁₄H₈O₉

Average Molecular Mass

320.208 g/mol

Monoisotopic Mass

320.017 g/mol

CAS Registry Number

Not Available

IUPAC Name

3,4,8,9,10-pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid

Traditional Name

3,4,8,9,10-pentahydroxy-6-oxobenzo[c]chromene-1-carboxylic acid

SMILES

OC(=O)C1=CC(O)=C(O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2

InChI Identifier

InChI=1S/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21)

InChI Key

FLZGFQFYDGHWLR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
7,8-dihydroxycoumarin
Gallic acid or derivatives
Isocoumarin
Dihydroxybenzoic acid
Coumarin
Benzopyran
Hydroxybenzoic acid
1-benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.57 g/L	ALOGPS
logP	1.97	ALOGPS
logP	1.72	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.1 m³·mol⁻¹	ChemAxon
Polarizability	27.86 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	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-00ku-1001019000-bc25f4f4a567436b1b48	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f96-0292000000-9abe0367bba3a23ecd66	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_5_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_5_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_5_5) - 70eV, Positive	Not Available	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 ("3,4,8,9,10-pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid,3TBDMS,#10" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0039000000-82695d9322f4dbeec5c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fi0-0095000000-27f2b579b0f1622089be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-0090000000-d01e9d37d6087dbb8901	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-0069000000-81f895d7567d3be07107	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00or-0093000000-46f6e09cc1786341ef8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-11wc-1490000000-fe99935c39f048ce975e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-c56cd78169095ff1d6e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016r-0096000000-96219b6b895017ea4d34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldm-0290000000-3511c6e68423f6bece35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0009000000-9b7b9d24151bda5b0ee9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-10c9d87708ef73061519	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02ea-0090000000-c67b5f063aac18a05ccd	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

HMDB0126633

FooDB ID

FDB006735

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

4477499

ChEBI ID

Not Available

PubChem Compound ID

5319108

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis)

Luteic acid (CHEM026203)

Structure for CHEM026203: Luteic acid