Showing Compound S-(Hydroxymethyl)glutathione (FDB023393)

Record Information

Version

1.0

Creation date

2011-09-21 00:29:16 UTC

Update date

2020-09-17 15:39:19 UTC

Primary ID

FDB023393

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

S-(Hydroxymethyl)glutathione

Description

S-(Hydroxymethyl)glutathione, also known as sergsh, 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. S-(Hydroxymethyl)glutathione is a very strong basic compound (based on its pKa). An S-substituted glutathione that is glutathione in which the mercapto hydrogen has been replaced by a hydroxymethyl group. S-(Hydroxymethyl)glutathione exists in all living species, ranging from bacteria to humans.

CAS Number

32260-87-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrate	Generator, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrIC ACID	ChEBI, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyrate	Generator, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyric acid	Generator, HMDB
Formaldehyde-glutathione thiohemiacetal	HMDB
Glutathione-formaldehyde thiohemiacetal	HMDB
L-gamma-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycine	HMDB
L-γ-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycine	HMDB
S-(Hydroxymethyl)glutathione	HMDB
S-Hydroxymethyl-glutathione	HMDB

Showing 1 to 10 of 12 entries

Predicted Properties

Property	Value	Source
Water Solubility	5.27 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-5.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.05 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	75.2 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	0	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

C11H19N3O7S

IUPAC name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid

InChI Identifier

InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1

InChI Key

PIUSLWSYOYFRFR-BQBZGAKWSA-N

Isomeric SMILES

N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O

Average Molecular Weight

337.349

Monoisotopic Molecular Weight

337.094370667

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
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Fatty acid
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Sulfenyl compound
Carboxylic acid
Organopnictogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organic oxide
Primary amine
Organosulfur compound
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutathione derivative (CHEBI:48926 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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

Type	Description	Splash Key	View
Predicted GC-MS	S-(Hydroxymethyl)glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01po-6291000000-700a78b68cd3c72dace0	Spectrum
Predicted GC-MS	S-(Hydroxymethyl)glutathione, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ukl-9410370000-758e7d3d20ef5e803fa9	Spectrum
Predicted GC-MS	S-(Hydroxymethyl)glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00du-0195000000-0fb852c5aa71ebfacbc3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0570-4690000000-74c4fbcadf9e75cea5e6	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4920000000-a75d217a2989134725ab	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-5089000000-0963b985ed393a77403b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05di-5393000000-80626db3d68b3e84d33f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-9200000000-c770bc62700bd5b4872c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0029000000-9285be543171793a7f61	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-1941000000-3b0ed9e0505deb83df54	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9400000000-cdcded7632edf6274abf	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05g0-0193000000-b9ae6fff6991f7a74ac1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-9440000000-4e976999daadff083f1c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-9400000000-49e525bdebda32941d94	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

394301

ChEMBL ID

Not Available

KEGG Compound ID

C14180

Pubchem Compound ID

447123

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04662

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

AHE

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

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound S-(Hydroxymethyl)glutathione (FDB023393)

Structure for FDB023393 (S-(Hydroxymethyl)glutathione)