Glutathione

Details

• Internal ID: 3506e9d6-d109-43f6-9887-4cd8b56fd8d0
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides
• IUPAC Name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• SMILES (Canonical): C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
• SMILES (Isomeric): C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
• 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)/t5-,6-/m0/s1
• InChI Key: RWSXRVCMGQZWBV-WDSKDSINSA-N
• Popularity: 151,808 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₇N₃O₆S
• Molecular Weight: 307.33 g/mol
• Exact Mass: 307.08380644 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: -4.50
• Atomic LogP (AlogP): -2.21
• H-Bond Acceptor: 6
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• 70-18-8
• L-Glutathione
• Glutathion
• Isethion
• L-Glutathione reduced
• Tathion
• Glutathione-SH
• reduced glutathione
• Glutinal
• Tathione
• Deltathione
• Neuthion
• Copren
• Glutide
• Triptide
• Ledac
• Glutatione
• GSH
• Glutatiol
• Panaron
• Glutathione SH
• L-Glutatione
• Glutathione (reduced)
• glutathione reduced
• gamma-L-Glutamyl-L-cysteinylglycine
• Agifutol S
• gamma-L-glutamyl-L-cysteinyl-glycine
• Glutathione [JAN]
• 5-L-Glutamyl-L-cysteinylglycine
• Glutham
• Aec glutathione
• L-Glutathione, reduced
• L-gamma-glutamyl-L-cysteinylglycine
• gamma-L-Glutamylcysteinylglycine
• Reduced l-glutathione
• CCRIS 2094
• glutathione red
• red. glutathione
• Bakezyme RX
• N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine
• N-(N-L-gamma-Glutamyl-L-cysteinyl)glycine
• UNII-GAN16C9B8O
• EINECS 200-725-4
• GAN16C9B8O
• glycine, N-(N-L-gamma-glutamyl-L-cysteinyl)-
• NSC 400639
• L-Glutathione reduce
• Glycine, L-gamma-glutamyl-L-cysteinyl-
• (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• (S)-2-Amino-5-(((R)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)amino)-5-oxopentanoic acid
• DTXSID6023101
• C10H17N3O6S
• CHEBI:16856
• Glutathione [BAN:JAN]
• Glutathione (Reduced type)
• L-glutamyl-L-cysteinylglycine
• L-Glutathione (reduced form)
• Glycine, L-.gamma.-glutamyl-L-cysteinyl-
• DTXCID903101
• BenzenaMine, 2-[(4-Methoxyphenyl)Methoxy]-
• (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid
• 106272-20-2
• 95687-20-0
• GLUTATHIONE (II)
• GLUTATHIONE [II]
• N-(N-L-.gamma.-Glutamyl-L-cysteinyl)glycine
• N5-((R)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)-L-glutamine
• GLUTATHIONE (MART.)
• GLUTATHIONE [MART.]
• GLUTATHIONE (USP-RS)
• GLUTATHIONE [USP-RS]
• [Glu(-Cys)]n-Gly
• GLUTATHIONE (EP MONOGRAPH)
• GLUTATHIONE [EP MONOGRAPH]
• MFCD00065939
• NSC400639
• CAS-70-18-8
• (S)-2-Amino-5-((R)-1-(carboxymethylamino)-3-mercapto-1-oxopropan-2-ylamino)-5-oxopentanoic acid
• Glutathione, Reduced
• SR-05000002567
• gamma L Glu L Cys Gly
• gamma-L-Glu-L-Cys-Gly
• L-Glutathione reduced form
• phytochelatins
• ReadiSorb
• Glutathione;
• 1lbk
• NCGC00094976-01
• gamma L Glutamyl L Cysteinylglycine
• Tathion (TN)
• Glutathione (JP17)
• Spectrum_000419
• 1oe7
• 1oe8
• 1r4w
• C(N-.gamma.Glu-)G
• Glycine, N-(N-L-.gamma.-glutamyl-L-cysteinyl)-
• GLUTATHIONE [MI]
• Reduced Glutathione,(S)
• Spectrum2_001500
• Spectrum3_000946
• Spectrum4_001056
• Spectrum5_000940
• ?-Glutamylcysteinylglycine
• Glutathione, Reduced Form
• GLUTATHIONE [INCI]
• bmse000185
• bmse000952
• bmse000956
• D02HFD
• GLUTATHIONE [VANDF]
• Cys(N-.gamma.Glu-)-Gly
• SCHEMBL9167
• CHEMBL1543
• GLUTATHIONE [WHO-DD]
• KBioGR_001352
• KBioSS_000899
• MLS001333069
• DivK1c_000075
• SPECTRUM1502248
• SPBio_001519
• gamma-glutamyl-cysteinyl-glycine
• GTPL6737
• ?-L-Glutamyl-L-cysteinylglycine
• L-?-glutamyl-L-cysteinylglycine
• L-Glutathione reduced, 97.0%
• CHEBI:60836
• HMS500D17
• KBio1_000075
• KBio2_000899
• KBio2_003467
• KBio2_006035
• KBio3_002012
• (gamma-Glutamylcysteine)n-glycine
• L-g-glutamyl-L-cysteinyl-glycine
• y-L-Glutamyl-L-cysteinyl-glycine
• L-?-glutamyl-L-cysteinyl-glycine
• NINDS_000075
• HMS1921N22
• Pharmakon1600-01502248
• HY-D0187
• L-Glutathione reduced, >=98.0%
• gam.-L-Glutamyl-L-cysteinyl-glycine
• Tox21_111371
• BDBM50422268
• C10-H17-N3-O6-S
• CCG-38876
• L-gamma-glutamyl-L-cysteinyl-glycine
• NSC758199
• s4606
• AKOS015999135
• Tox21_111371_1
• CS-7948
• DB00143
• Glicina, l-gamma-glutamil-l-cisteinil-
• NSC-758199
• SDCCGMLS-0066687.P001
• .gamma.-L-Glutamyl-L-cysteinyl-glycine
• IDI1_000075
• N-(N-L-?-Glutamyl-L-cysteinyl)glycine
• Pharm Biol 11: 539 (1968)
• SMP1_000247
• NCGC00264046-02
• DS-14675
• GSH;gamma-L-Glutamyl-L-cysteinyl-glycine
• LS-72665
• SMR000857220
• SBI-0051743.P002
• L-Glutathione reduced, BioXtra, >=98.0%
• G0074
• Glycine, N-(N-L-?-glutamyl-L-cysteinyl)-
• Glycine, N-(N-L-gamma-glutamyl-L-cysteinyl)
• C00051
• C02471
• D00014
• EN300-311690
• G-3980
• P19615
• AB00443568_03
• Glutathione 100 microg/mL in Acetonitrile:Water
• A866658
• Q116907
• SR-05000002567-1
• SR-05000002567-2
• L-Glutathione reduced, Vetec(TM) reagent grade, >=98%
• Z2183947556
• Glutathione, European Pharmacopoeia (EP) Reference Standard
• Glutathione, United States Pharmacopeia (USP) Reference Standard
• Glutathione, Pharmaceutical Secondary Standard; Certified Reference Material
• L-Glutathione reduced, cell culture tested, BioReagent, >=98.0%, powder
• (2S)-2-Amino-4-(1-(carboxymethyl)carbamoyl-(2R)-2-sulfanylethylcarbamoyl)butanoic acid
• (2S)-2-AMINO-4-{[(1R)-1-[(CARBOXYMETHYL)CARBAMOYL]-2-SULFANYLETHYL]CARBAMOYLBUTANOIC ACID
• (2S)-2-Amino-5-({(2R)-1-[(carboxymethyl)amino]-1-oxo-3-sulfanyl-2-propanyl}amino)-5-oxopentanoic acid
• glutathione; l-glutathione reduced; 5-l-glutamyl-l-cysteinylglycine; gamma-l-glutamyl-l-cysteinylglycine; gsh

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8377	83.77%
Caco-2	-	0.9356	93.56%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5536	55.36%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9478	94.78%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9395	93.95%
P-glycoprotein inhibitior	-	0.9499	94.99%
P-glycoprotein substrate	-	0.8679	86.79%
CYP3A4 substrate	-	0.6040	60.40%
CYP2C9 substrate	-	0.6240	62.40%
CYP2D6 substrate	-	0.7955	79.55%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9179	91.79%
CYP2C19 inhibition	-	0.9190	91.90%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.9437	94.37%
CYP2C8 inhibition	-	0.9469	94.69%
CYP inhibitory promiscuity	-	0.9898	98.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.7183	71.83%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9870	98.70%
Skin irritation	-	0.8365	83.65%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	+	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7815	78.15%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.8149	81.49%
skin sensitisation	-	0.9338	93.38%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.9222	92.22%
Acute Oral Toxicity (c)	III	0.6713	67.13%
Estrogen receptor binding	-	0.5426	54.26%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.6097	60.97%
Glucocorticoid receptor binding	+	0.5418	54.18%
Aromatase binding	-	0.8089	80.89%
PPAR gamma	+	0.6870	68.70%
Honey bee toxicity	-	0.9295	92.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.9148	91.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.69%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.89%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.62%	90.17%
CHEMBL236	P41143	Delta opioid receptor	96.34%	99.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.55%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	93.95%	92.29%
CHEMBL1255126	O15151	Protein Mdm4	93.35%	90.20%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.53%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.25%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.29%	96.95%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	89.03%	100.00%
CHEMBL230	P35354	Cyclooxygenase-2	88.67%	89.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.93%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	86.76%	91.19%
CHEMBL3784	Q09472	Histone acetyltransferase p300	85.91%	93.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.76%	96.09%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	84.15%	82.86%
CHEMBL233	P35372	Mu opioid receptor	83.94%	97.93%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	83.70%	97.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.35%	96.47%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	82.25%	96.28%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.18%	89.50%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	81.40%	89.33%

Plants that contains it

• Allium cepa
• Allium sativum
• Aloe africana
• Arabidopsis thaliana
• Brassica oleracea
• Phaseolus vulgaris

Cross-Links

• PubChem: 124886
• NPASS: NPC174304
• ChEMBL: CHEMBL1543
• LOTUS: LTS0008500
• wikiData: Q116907