P. aeruginosa Metabolome Database: glutathione (PAMDB110431)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB110431

Identification

Name:

glutathione

Description:

A peptide anion obtained by deprotonation of both carboxy groups and protonation of the glutamyl amino group of glutathione; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

γ-L-glutamyl-L-cysteinyl-glycine
GSH
reduced glutathione
glutathionate

Chemical Formula:

C₁₀H₁₆N₃O₆S

Average Molecular Weight:

306.31

Monoisotopic Molecular Weight:

308.091631016

InChI Key:

RWSXRVCMGQZWBV-WDSKDSINSA-M

InChI:

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)/p-1/t5-,6-/m0/s1

CAS number:

70-18-8

IUPAC Name:

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

Traditional IUPAC Name:

glutathione

SMILES:

C(S)C(C(NCC([O-])=O)=O)NC(=O)CCC([N+])C([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as peptides. These 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

Chemical entities

Super Class

Organic compounds

Class

Organic acids and derivatives

Sub Class

Carboxylic acids and derivatives

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 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

195 °C

Experimental Properties:

Property	Value	Reference
Melting Point	195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	292.5 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

S0 + glutathione → S-sulfanylglutathione
S-sulfanylglutathione + FE+3 + Water → Hydrogen ion + Sulfite + glutathione + FE+2
Selenite + AMP + glutathione disulfide + Hydrogen ion → adenosine 5'-phosphoselenate + glutathione
Selenite + glutathione + Hydrogen ion → selenodiglutathione + glutathione disulfide + Water
glutathione + 4-hydroxy-2-nonenal → 4-hydroxy-2-nonenal-glutathione conjugate
glutathione + Amino-Acids-20 → Cysteinylglycine + 5-L-GLUTAMYL-L-AMINO-ACID
1-chloro-2,4-dinitrobenzene + glutathione → Hydrogen ion + 2,4-dinitrophenyl-S-glutathione + Chloride
glutathione + Intracellular-Sulfur → S-sulfanylglutathione
A-LIPID-HYDROPEROXIDE + glutathione + Hydrogen ion → Lipids + glutathione disulfide + Water
selenodiglutathione + NADPH → glutathioselenol + glutathione + NADP+
2-hydroxyacyl-glutathiones + Water → glutathione + 2-Hydroxy-carboxylates
glutathioselenol + NADPH + Hydrogen ion → Hydrogen selenide + glutathione + NADP+

Pathways:

Arachidonic Acid Metabolism pae00590
Glutamate Metabolism pae00250
Glutathione Metabolism pae00480
Pyruvate Metabolism pae00620

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-0a4i-0900000000-5841845f736f9a667622	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)	splash10-0a4i-0900000000-bdecde153761cb67852e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-3795000000-d019cd7dcbad1f8a9e78	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9400000000-a83bf6292d41988256e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-305a92f8a9ffea58fa0e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009000000-e950bfc5867b391c6960	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0910000000-83f6c079d1112e74ecf4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-003r-0910000000-5b243cf8bd357ab270b1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009000000-29ef335479f56b620d88	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0009001000-d1f5986166efa523d024	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-056s-0495300000-dba7be381fd1ef776527	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0920000000-de5b8a5a377324599b39	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-053r-0007920000-7500cef211e48c8ea244	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0119003000-4eb7ed4e2a4cf6a83c66	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uki-0290000000-6893386899c6eed6a1a6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-05g0-0190000000-cacc2de4ab18ed59798b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0009000000-6b4268add43ab66ef015	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-08fr-0015009000-a01bdc13a34d6ce8416f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0uki-0290000000-ea94ec8247b4e025adbe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0039210000-e1f721157a9ea89959d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a59-0039210000-35ce450ea95922abf0e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0009000000-9b01fba547d1fcde113a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0952000000-4a2a42699cf4aab2c559	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-002f-2900000000-bd9ba27b48b1322b7618	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004m-5900000000-cc7184d5bba50e6e49d0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9200000000-aecd0eb18a10c3ffb7ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Uotila L (1973)Preparation and assay of glutathione thiol esters. Survey of human liver glutathione thiol esterases. Biochemistry 12, Pubmed: 4200890
Uotila L (1973)Purification and characterization of S-2-hydroxyacylglutathione hydrolase (glyoxalase II) from human liver. Biochemistry 12, Pubmed: 4745654

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CAS	70-18-8
ChEBI	57925
ChemSpider	19589806
HMDB	HMDB00125
IAF1260	33669
KEGG	C00051
KNApSAcK	C00001518
MetaboLights	MTBLC57925
PubChem	20756463

glutathione (PAMDB110431)

Structure for glutathione (PAMDB110431)