ChemFOnt: Showing chemical card for 2-S-Glutathionyl caftaric acid (CFc000281229)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:24 UTC

Chemfont ID

CFc000281229

Molecule Identification

Common Name

2-S-Glutathionyl caftaric acid

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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
2-S-Glutathionyl caftarate	Generator

Chemical Formula

C₂₃H₂₇N₃O₁₅S

Average Molecular Weight

617.537

Monoisotopic Molecular Weight

617.116287899

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

Traditional Name

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

CAS Registry Number

None

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

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

Chemical Taxonomy

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

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301713)

Food

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Fruit

Berry

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

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

External Links

HMDB ID

HMDB0301713

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000246

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

117842555

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-S-Glutathionyl caftaric acid (CFc000281229)

MOL for CFc000281229 (2-S-Glutathionyl caftaric acid)

3D MOL for CFc000281229 (2-S-Glutathionyl caftaric acid)

3D SDF for CFc000281229 (2-S-Glutathionyl caftaric acid)

3D-SDF for CFc000281229 (2-S-Glutathionyl caftaric acid)

PDB for CFc000281229 (2-S-Glutathionyl caftaric acid)

3D PDB for CFc000281229 (2-S-Glutathionyl caftaric acid)

SMILES for CFc000281229 (2-S-Glutathionyl caftaric acid)

INCHI for CFc000281229 (2-S-Glutathionyl caftaric acid)

Structure for CFc000281229 (2-S-Glutathionyl caftaric acid)

3D Structure for CFc000281229 (2-S-Glutathionyl caftaric acid)