Glutathione Disulfide

Details

• Internal ID: 0274893b-69b6-4d5e-b8bf-70663c392906
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides
• IUPAC Name: (2S)-2-amino-5-[[(2R)-3-[[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
• InChI Key: YPZRWBKMTBYPTK-BJDJZHNGSA-N
• Popularity: 16,443 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂N₆O₁₂S₂
• Molecular Weight: 612.60 g/mol
• Exact Mass: 612.15196282 g/mol
• Topological Polar Surface Area (TPSA): 368.00 Ų
• XlogP: -9.10
• Atomic LogP (AlogP): -3.88
• H-Bond Acceptor: 12
• H-Bond Donor: 10
• Rotatable Bonds: 21

Synonyms

• glutathione disulfide
• 27025-41-8
• GSSG
• Glutathione disulphide
• Oxigluthione
• Glutathione-ssg
• Glutathone disulfide
• Bi(glutathion-S-yl)
• L(-)-Glutathione
• Oxiglutatione [INN]
• S,S'-Ethylenebis(glutathione)
• Oxiglutationum [INN-Latin]
• Oxiglutationa [INN-Spanish]
• CCRIS 780
• Bis(gamma-glutamyl-L-cysteinylglycine) disulfide
• Glutamine, N,N'-(dithiobis(1-((carboxymethyl)carbamoyl)ethylene))di-, L-
• N-(N-gamma-Glutamyl-cysteinyl)glycine-(2,2)-disulfide
• ULW86O013H
• Glycine, L-gamma-glutamyl-L-cysteinyl-, (2,2')-disulfide
• DTXSID5048972
• CHEBI:17858
• glutathione ox
• N,N'-(Dithiobis((R)-1-((carboxymethyl)carbamoyl)ethylene))di-L-glutamine
• Oxiglutationa
• Oxiglutationum
• MFCD00063106
• (2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• (2S,2'S)-5,5'-(((2R,2'R)-disulfanediylbis(1-((carboxymethyl)amino)-1-oxopropane-3,2-diyl))bis(azanediyl))bis(2-amino-5-oxopentanoic acid)
• GDS
• EINECS 248-170-7
• Glutathione-S-S-glutathione
• UNII-ULW86O013H
• Navstel
• ox. glutathione
• 121-24-4
• Glutathione (TN)
• NCGC00164484-02
• oxidised glutathione
• Sleep-promoting factor B
• Oxiglutatione (JAN/INN)
• bmse000170
• bmse000806
• bmse000906
• OXIGLUTATIONE [JAN]
• CHEMBL1372
• GLUTATHIONE, DISULFIDE
• SCHEMBL138746
• OXIGLUTATIONE [WHO-DD]
• GTPL6835
• DTXCID8028898
• BDBM225231
• GLUTATHIONE DISULFIDE [MI]
• OXIGLUTATIONE [ORANGE BOOK]
• (2S)-2-amino-5-[[(2R)-3-[[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• HY-D0844
• Tox21_113423
• s3743
• AKOS015902226
• BCP9000564
• CCG-270238
• CS-8140
• DB03310
• NCGC00142600-01
• NCGC00142600-03
• (2S,2'S)-5,5'-(2R,2'R)-3,3'-disulfanediylbis(1-(carboxymethylamino)-1-oxopropane-3,2-diyl)bis(azanediyl)bis(2-amino-5-oxopentanoic acid)
• 4-{N-[(1R)-2-({(2R)-2-((4S)-4-amino-4-carboxybutanoylamino)-2-[N-(carboxymethy l)carbamoyl]ethyl}disulfanyl)-1-[N-(carboxymethyl)carbamoyl]ethyl]carbamoyl}(2 S)-2-aminobutanoic acid
• AC-37033
• AS-14770
• GLUTATHIONE DISULFIDE [ORANGE BOOK]
• SBI-0207031.P001
• CAS-27025-41-8
• L-gamma-glutamyl-L-cysteinyl-glycine disulfide
• C00127
• D00031
• F20504
• EN300-7372307
• A877046
• Q3324838
• (gamma-Glu-Cys-Gly) (gamma-Glu-Cys-Gly) [Disulfide bridge: 2a-2b]
• Glycine, L-.gamma.-glutamyl-L-cysteinyl-, bimol. (2->2')-disulfide
• Glycine, L-g-glutamyl-L-cysteinyl-, bimol. (2~2')-disulfide (9CI)
• Glycine, L-gamma-glutamyl-L-cysteinyl-, bimol. (2.fwdarw.2')-disulfide
• Glutamine, N,N'-[dithiobis[1-[(carboxymethyl)carbamoyl]ethylene]]di- (7CI)
• Glutamine, N,N'-[dithiobis[1-[(carboxymethyl)carbamoyl]ethylene]]di-, L- (8CI)
• (2S)-2-amino-5-[[(1R)-1-[[[(2R)-2-[[(4S)-4-amino-4-carboxy-butanoyl]amino]-3-(carboxymethylamino)-3-keto-propyl]disulfanyl]methyl]-2-(carboxymethylamino)-2-keto-ethyl]amino]-5-keto-valeric acid
• (2S)-2-azaniumyl-4-{[(1R)-2-{[(2R)-2-[(4S)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoate
• (2S)-2-azanyl-5-[[(2R)-3-[[(2R)-2-[[(4S)-4-azanyl-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]-3-(2-hydroxy-2-oxoethylamino)-3-oxidanylidene-propyl]disulfanyl]-1-(2-hydroxy-2-oxoethylamino)-1-oxidanylidene-propan-2-yl]amino]-5-oxidanylidene-pentanoic acid
• (2S,2'S)-5,5'-(((2R,2'R)-disulfanediylbis(1-((carboxymethyl)amino)-1-oxopropane-3,2-diyl))bis(azanediyl))bis(2-amino-5-oxopentanoicacid)
• (2S,2'S)-5,5'-[disulfanediylbis({(2R)-3-[(carboxymethyl)amino]-3-oxopropane-1,2-diyl}imino)]bis(2-amino-5-oxopentanoic acid)
• (2S,2'S)-5,5'-[disulfanediylbis({(2R)-3-[(carboxymethyl)amino]-3-oxopropane-1,2-diyl}imino)]bis(2-amino-5-oxopentanoic acid) (non-preferred name)
• 2-AMINO-5-((1-((CARBOXYMETHYL)AMINO)-3-MERCAPTO-1-OXOPROPAN-2-YL)AMINO)-5-OXOPENTANOIC ACID
• 4-{N-[(1R)-2-({(2R)-2-((4S)-4-Amino-4-carboxybutanoylamino)-2-[N-(carboxymethyl)carbamoyl]ethyl}disulfanyl)-1-[N-(carboxymethyl)carbamoyl]ethyl]carbamoyl}(2S)-2-aminobutanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7098	70.98%
Caco-2	-	0.8897	88.97%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6796	67.96%
OATP2B1 inhibitior	+	0.5663	56.63%
OATP1B1 inhibitior	+	0.9401	94.01%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8859	88.59%
P-glycoprotein inhibitior	+	0.6708	67.08%
P-glycoprotein substrate	-	0.8854	88.54%
CYP3A4 substrate	-	0.5791	57.91%
CYP2C9 substrate	-	0.6211	62.11%
CYP2D6 substrate	-	0.8070	80.70%
CYP3A4 inhibition	-	0.8874	88.74%
CYP2C9 inhibition	-	0.8857	88.57%
CYP2C19 inhibition	-	0.8615	86.15%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.9373	93.73%
CYP2C8 inhibition	-	0.9251	92.51%
CYP inhibitory promiscuity	-	0.9907	99.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6700	67.00%
Carcinogenicity (trinary)	Non-required	0.6521	65.21%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.8721	87.21%
Skin irritation	-	0.8260	82.60%
Skin corrosion	-	0.9522	95.22%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5223	52.23%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6701	67.01%
skin sensitisation	-	0.9243	92.43%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.6224	62.24%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.8789	87.89%
Acute Oral Toxicity (c)	III	0.7989	79.89%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5599	55.99%
Glucocorticoid receptor binding	-	0.4887	48.87%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.6224	62.24%
Honey bee toxicity	-	0.9087	90.87%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.6269	62.69%

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	99.97%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.90%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.06%	90.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	96.05%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.81%	99.17%
CHEMBL236	P41143	Delta opioid receptor	95.05%	99.35%
CHEMBL1255126	O15151	Protein Mdm4	91.29%	90.20%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.14%	97.21%
CHEMBL230	P35354	Cyclooxygenase-2	89.61%	89.63%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.22%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.12%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.98%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.95%	91.11%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.72%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.49%	94.45%
CHEMBL233	P35372	Mu opioid receptor	86.09%	97.93%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.33%	89.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.62%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.80%	93.56%
CHEMBL2514	O95665	Neurotensin receptor 2	80.22%	100.00%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	80.21%	96.28%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 65359
• LOTUS: LTS0023221
• wikiData: Q3324838