AFCDB: Glutathione (FDB001498)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:59 UTC

Update date

2020-09-17 15:38:20 UTC

Primary ID

FDB001498

Secondary Accession Numbers

FDB003866

Chemical Information

FooDB Name

Glutathione

Description

Glutathione, also known as GSH or agifutol S, 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. Glutathione is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Glutathione is a very strong basic compound (based on its pKa). A tripeptide compound consisting of glutamic acid attached via its side chain to the N-terminus of cysteinylglycine. Glutathione exists in all living species, ranging from bacteria to humans. Within humans, glutathione participates in a number of enzymatic reactions. In particular, leukotriene A4 and glutathione can be converted into leukotriene C4 through its interaction with the enzyme leukotriene C4 synthase. In addition, 15(S)-hpete and glutathione can be converted into 15(S)-hete and oxidized glutathione through its interaction with the enzyme glutathione peroxidase 1. In humans, glutathione is involved in mefenamic acid action pathway. Outside of the human body, Glutathione is found, on average, in the highest concentration within a few different foods, such as purslanes, spinachs, and corns. Glutathione has also been detected, but not quantified in, several different foods, such as yautia, coconuts, common salsifies, pigeon pea, and ohelo berries. This could make glutathione a potential biomarker for the consumption of these foods. Glutathione is a potentially toxic compound.

CAS Number

70-18-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-4.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	69.11 m³·mol⁻¹	ChemAxon
Polarizability	29.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H17N3O6S

IUPAC name

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

InChI Identifier

InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

InChI Key

RWSXRVCMGQZWBV-WDSKDSINSA-N

Isomeric SMILES

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

Average Molecular Weight

307.323

Monoisotopic Molecular Weight

307.083805981

Classification

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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid or derivatives
Amino acid
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thiol (CHEBI:16856 )
L-cysteine derivative (CHEBI:16856 )
tripeptide (CHEBI:16856 )
Coenzymes (C00051 )

Ontology

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Industrial application:

Personal care products

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	195 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Glutathione, x TMS, GC-MS Spectrum	splash10-0a4i-0900000000-5841845f736f9a667622	Spectrum
GC-MS	Glutathione, x TMS, GC-MS Spectrum	splash10-0a4i-0900000000-bdecde153761cb67852e	Spectrum
GC-MS	Glutathione, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-5841845f736f9a667622	Spectrum
GC-MS	Glutathione, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-bdecde153761cb67852e	Spectrum
GC-MS	Glutathione, non-derivatized, GC-MS Spectrum	splash10-0a4i-1910000000-52bc43dd913b68d74f84	Spectrum
GC-MS	Glutathione, non-derivatized, GC-MS Spectrum	splash10-08fs-3960000000-63ce34def2ae94b95515	Spectrum
GC-MS	Glutathione, non-derivatized, GC-MS Spectrum	splash10-0pb9-0921000000-88168b0a9f5fc5fead3f	Spectrum
Predicted GC-MS	Glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-7890000000-5853006f66d946dd3d2e	Spectrum
Predicted GC-MS	Glutathione, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0596-9112300000-e82cf72540c283d8e323	Spectrum
Predicted GC-MS	Glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glutathione, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-3795000000-d019cd7dcbad1f8a9e78	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9400000000-a83bf6292d41988256e3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-305a92f8a9ffea58fa0e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009000000-e950bfc5867b391c6960	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0910000000-83f6c079d1112e74ecf4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-003r-0910000000-5b243cf8bd357ab270b1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009000000-29ef335479f56b620d88	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009001000-d1f5986166efa523d024	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-056s-0495300000-dba7be381fd1ef776527	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0920000000-de5b8a5a377324599b39	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-053r-0007920000-7500cef211e48c8ea244	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0119003000-4eb7ed4e2a4cf6a83c66	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uki-0290000000-6893386899c6eed6a1a6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-05g0-0190000000-cacc2de4ab18ed59798b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0009000000-6b4268add43ab66ef015	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-08fr-0015009000-a01bdc13a34d6ce8416f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uki-0290000000-ea94ec8247b4e025adbe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0039210000-e1f721157a9ea89959d6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a59-0039210000-35ce450ea95922abf0e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0009000000-9b01fba547d1fcde113a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0952000000-4a2a42699cf4aab2c559	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-002f-2900000000-bd9ba27b48b1322b7618	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004m-5900000000-cc7184d5bba50e6e49d0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9200000000-aecd0eb18a10c3ffb7ab	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0729-4492000000-78a928563adf9038ba59	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16856

Phenol-Explorer ID

Not Available

DrugBank ID

DB00143

HMDB ID

HMDB00125

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Glutathione

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
anti cytotoxic	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
antidote	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti eczemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatitic	62868	Any compound that is able to prevent damage to the liver.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Glutathione synthetase	GSS	P48637
Glutathione S-transferase Mu 3	GSTM3	P21266
Glutathione S-transferase omega-1	GSTO1	P78417
Glutathione S-transferase A2	GSTA2	P09210
Glutathione S-transferase P	GSTP1	P09211
Glutathione S-transferase Mu 2	GSTM2	P28161
Glutathione S-transferase Mu 1	GSTM1	P09488
Glutathione S-transferase kappa 1	GSTK1	Q9Y2Q3
Microsomal glutathione S-transferase 3	MGST3	O14880
Glutathione S-transferase A1	GSTA1	P08263
Microsomal glutathione S-transferase 1	MGST1	P10620
Glutathione S-transferase Mu 4	GSTM4	Q03013
Glutathione S-transferase Mu 5	GSTM5	P46439
Microsomal glutathione S-transferase 2	MGST2	Q99735
Glutathione S-transferase A5	GSTA5	Q7RTV2
Glutathione S-transferase A3	GSTA3	Q16772
Glutathione S-transferase A4	GSTA4	O15217
Glutathione S-transferase omega-2	GSTO2	Q9H4Y5
Hematopoietic prostaglandin D synthase	HPGDS	O60760
Glutathione peroxidase 7	GPX7	Q96SL4
Epididymal secretory glutathione peroxidase	GPX5	O75715
Glutathione peroxidase 6	GPX6	P59796
Glutathione peroxidase 1	GPX1	P07203
Phospholipid hydroperoxide glutathione peroxidase, mitochondrial	GPX4	P36969
Glutathione peroxidase 3	GPX3	P22352
Glutathione peroxidase 2	GPX2	P18283
Prostaglandin E synthase	PTGES	O14684
Peroxiredoxin-6	PRDX6	P30041
S-formylglutathione hydrolase	ESD	P10768
Gamma-glutamyltranspeptidase 1	GGT1	P19440
Gamma-glutamyltransferase 7	GGT7	Q9UJ14
Leukotriene C4 synthase	LTC4S	Q16873
Maleylacetoacetate isomerase	GSTZ1	O43708
Glutaredoxin-1	GLRX	P35754
Glutaredoxin-2, mitochondrial	GLRX2	Q9NS18
Gamma-glutamyltransferase 6	GGT6	Q6P531
Thioredoxin domain-containing protein 12	TXNDC12	O95881
Gamma-glutamyltransferase 5	GGT5	P36269
Glutathione S-transferase theta-2	GSTT2	P0CG29

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Glutathione (FDB001498)

Structure for FDB001498 (Glutathione)