ChemFOnt: Showing chemical card for Glutathionyl-3-hydroxykynurenine glucoside (CFc000042883)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:38 UTC

Chemfont ID

CFc000042883

Molecule Identification

Common Name

Glutathionyl-3-hydroxykynurenine glucoside

Definition

Glutathionyl-3-hydroxykynurenine glucoside (GSH-3-OHKG) is a fluorophore and UV filter compound isolated from human lenses. The UV filter compounds present in lenses are thought to protect the lens and retina from UV-induced photodamage and/or to reduce chromatic aberration. Unlike the other UV filter compounds, 3-hydroxykynurenine glucoside (3-OHKG) and 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside (AHBG), which remain relatively stable or decrease slightly in concentration during adult life, GSH-3-OHKG was found to increase in relative concentration with age (PMID: 10409626 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
GSH-3-OHKG	HMDB

Chemical Formula

C₂₆H₃₆N₄O₁₅S

Average Molecular Weight

676.65

Monoisotopic Molecular Weight

676.189787649

IUPAC Name

(2S)-2-amino-4-{[(1R)-2-{[(1S)-3-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-carboxy-3-oxopropyl]sulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1R)-2-{[(1S)-3-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-carboxy-3-oxopropyl]sulfanyl}-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

244286-41-7

SMILES

N[C@@H](CCC(=O)N[C@@H](CS[C@@H](CC(=O)C1=CC=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1N)C(O)=O)C(=O)NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C26H36N4O15S/c27-11(24(40)41)4-5-17(33)30-12(23(39)29-7-18(34)35)9-46-16(25(42)43)6-13(32)10-2-1-3-14(19(10)28)44-26-22(38)21(37)20(36)15(8-31)45-26/h1-3,11-12,15-16,20-22,26,31,36-38H,4-9,27-28H2,(H,29,39)(H,30,33)(H,34,35)(H,40,41)(H,42,43)/t11-,12-,15+,16-,20+,21-,22+,26+/m0/s1

InChI Key

MUWBOANXAOJPLO-ROWCEFMGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Saccharolipid
Phenolic glycoside
Alkyl-phenylketone
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Butyrophenone
L-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Phenylketone
Tricarboxylic acid or derivatives
Phenoxy compound
Aniline or substituted anilines
Aryl alkyl ketone
Aryl ketone
Phenol ether
Gamma-keto acid
Benzoyl
Thia fatty acid
Hydroxy fatty acid
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Keto acid
Monocyclic benzene moiety
Vinylogous amide
Amino acid
Secondary alcohol
Ketone
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Thioether
Polyol
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062471)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.53 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-6.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	338.59 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	153.17 m³·mol⁻¹	ChemAxon
Polarizability	65.12 Å³	ChemAxon
Number of Rings	2	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

HMDB0062471

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Glutathionyl-3-hydroxykynurenine glucoside (CFc000042883)

MOL for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

3D MOL for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

3D SDF for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

3D-SDF for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

PDB for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

3D PDB for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

SMILES for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

INCHI for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

Structure for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)

3D Structure for CFc000042883 (Glutathionyl-3-hydroxykynurenine glucoside)