Showing Compound gamma-Glutamyl-cysteine (FDB003603)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:52 UTC

Update date

2020-09-17 15:38:47 UTC

Primary ID

FDB003603

Secondary Accession Numbers

FDB030977

Chemical Information

FooDB Name

gamma-Glutamyl-cysteine

Description

gamma-Glutamylcysteine, also known as L-γ-glutamylcysteine or gamma-glu-cys, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is a very strong basic compound (based on its pKa). gamma-Glutamylcysteine exists in all living species, ranging from bacteria to humans. Outside of the human body, gamma-Glutamylcysteine has been detected, but not quantified in, several different foods, such as hyssops, rapes, black mulberries, red raspberries, and wild carrots. This could make gamma-glutamylcysteine a potential biomarker for the consumption of these foods. gamma-Glutamylcysteine is a potentially toxic compound. A molecular entity formed when L-cysteine amino group binds to the gamma-carbonyl of L-glutamic acid.

CAS Number

636-58-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(des-GLY)-glutathione	biospider
3GC	HMDB
5-L-Glutamyl-L-cysteine	ChEBI
5-L-Glutamylcysteine	HMDB
5-L-glutamylcysteine	biospider
g-Glu-cys	Generator
g-Glutamylcysteine	Generator
G-glutamylcysteine	biospider
g-L-Glutamyl-L-cysteine	Generator
G-l-glutamyl-l-cysteine	biospider

Showing 1 to 10 of 52 entries

Predicted Properties

Property	Value	Source
Water Solubility	2.62 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	56.31 m³·mol⁻¹	ChemAxon
Polarizability	23.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H14N2O5S

IUPAC name

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

InChI Identifier

InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

RITKHVBHSGLULN-WHFBIAKZSA-N

Isomeric SMILES

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

Average Molecular Weight

250.272

Monoisotopic Molecular Weight

250.062342258

Classification

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty acid
Dicarboxylic 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
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organosulfur compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylcysteine (CHEBI:17515 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Prostate

Cell and elements:

Cell:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Search:

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
GC-MS	gamma-Glutamyl-cysteine, non-derivatized, GC-MS Spectrum	splash10-054t-1920100000-5ce9a082971db6d9e2e9	Spectrum
GC-MS	gamma-Glutamyl-cysteine, non-derivatized, GC-MS Spectrum	splash10-054t-1920100000-5ce9a082971db6d9e2e9	Spectrum
Predicted GC-MS	gamma-Glutamyl-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053u-9630000000-344be03dbe2132b00c88	Spectrum
Predicted GC-MS	gamma-Glutamyl-cysteine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00b9-8494000000-88b1eea1e1badaee084b	Spectrum
Predicted GC-MS	gamma-Glutamyl-cysteine, non-derivatized, 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)	splash10-0udi-0090000000-50bd1555ededc1afde80	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0290000000-385ca433f03af7530f47	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9510000000-5f29ca903abe05256c83	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9510000000-5f29ca903abe05256c83	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1490000000-bfce673369358b8079e9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0690000000-c49357f0d28683125b6d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002b-2490000000-41c54aabf6acd4d3b53e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9050000000-1137fb3c62232376669c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1790000000-2aaa1344429a2297cc6b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4920000000-4ad42780853d5599c05b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9400000000-b67fd0eaf646aa8f47b3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-1390000000-e723899e4ca71bda7600	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sj-3960000000-9a2f96ad7d24e7546315	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9300000000-e14b428bbb5b63d3ae06	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0910000000-302a05e4e453b27bad64	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-3900000000-da869ba294aa1d1e7c49	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9100000000-4bc7ff3637ea175068f0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-0960000000-675f718188f5caad73ab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9600000000-13ddc5ab8de093dd11ab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-8b8a5550fa1112649784	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 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, 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, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum