Showing Compound 2-S-Glutathionyl caftaric acid (FDB000246)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:29 UTC

Update date

2019-11-26 02:54:35 UTC

Primary ID

FDB000246

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-S-Glutathionyl caftaric acid

Description

2-s-glutathionyl caftaric acid is a member of the class of compounds known as oligopeptides. Oligopeptides are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 2-s-glutathionyl caftaric acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 2-s-glutathionyl caftaric acid can be found in common grape, grape wine, and vinegar, which makes 2-s-glutathionyl caftaric acid a potential biomarker for the consumption of these food products.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-S-Glutathionyl caftarate	Generator
2-{[(2E)-3-[2-({2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}sulfanyl)-3,4-dihydroxyphenyl]prop-2-enoyl]oxy}-3-hydroxybutanedioate	Generator
2-{[(2E)-3-[2-({2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}sulphanyl)-3,4-dihydroxyphenyl]prop-2-enoyl]oxy}-3-hydroxybutanedioate	Generator
2-{[(2E)-3-[2-({2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}sulphanyl)-3,4-dihydroxyphenyl]prop-2-enoyl]oxy}-3-hydroxybutanedioic acid	Generator

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-4.6	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.67	ChemAxon
pKa (Strongest Basic)	8.92	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	320.41 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	137.38 m³·mol⁻¹	ChemAxon
Polarizability	56.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C23H27N3O15S

IUPAC name

2-{[(2E)-3-(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

InChI Identifier

InChI=1S/C23H27N3O15S/c24-10(21(35)36)3-5-13(28)26-11(20(34)25-7-14(29)30)8-42-19-9(1-4-12(27)16(19)32)2-6-15(31)41-18(23(39)40)17(33)22(37)38/h1-2,4,6,10-11,17-18,27,32-33H,3,5,7-8,24H2,(H,25,34)(H,26,28)(H,29,30)(H,35,36)(H,37,38)(H,39,40)/b6-2+

InChI Key

FRUUTAANUZUTPG-QHHAFSJGSA-N

Isomeric SMILES

NC(CCC(=O)NC(CSC1=C(\C=C\C(=O)OC(C(O)C(O)=O)C(O)=O)C=CC(O)=C1O)C(=O)NCC(O)=O)C(O)=O

Average Molecular Weight

617.537

Monoisotopic Molecular Weight

617.116287899

Classification

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Pentacarboxylic acid or derivatives
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cinnamic acid ester
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cysteine or derivatives
Coumaric acid or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Aryl thioether
Thiophenol ether
Catechol
Styrene
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
1-hydroxy-4-unsubstituted benzenoid
Alkylarylthioether
Fatty acid ester
Alpha-hydroxy acid
Fatty amide
Fatty acyl
Hydroxy acid
Benzenoid
Monosaccharide
N-acyl-amine
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Amino acid
Carboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Sulfenyl compound
Thioether
Carboxylic acid
Organooxygen compound
Organosulfur compound
Carbonyl group
Primary amine
Organic nitrogen compound
Alcohol
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-4411696000-7d36b29438beacf2bed7	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9202330000-8ee1a43a6e86ea0dbe4d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9221000000-c4480624c637a8c55984	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00yi-2312291000-ef2b1fca5415640378a0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0015-4596450000-7e7e4c9f0f9d29d1da9d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4592100000-bae959e051ff91c3be08	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0012292000-fa830efb487f1acd754e	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abc-0207930000-971ebbf052777c6ea77d	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9410100000-42c9a1c38fb677959e64	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-3010291000-ec024181e3a0741bbfa5	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-6900340000-b4172e1385a3fc697f0a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-6900000000-3ad23761b647ff689673	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

477

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Common grape	0.000 - 0.607 mg/100 g	0.35920 mg/100 g	PHENOL EXPLORER
Grape wine	0.42300 - 0.42300 mg/100 g	0.42300 mg/100 g	PHENOL EXPLORER
Vinegar	0.05854 - 0.05854 mg/100 g	0.05854 mg/100 g	PHENOL EXPLORER