Details of the Drug

General Information of Drug (ID: DM9EQC0)

Drug Name

Oxidized glutathione

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Approved	[1]
Bacterial infection	1A00-1C4Z	Investigative	[2]
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Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

612.6

Logarithm of the Partition Coefficient (xlogp)

-9.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H32N6O12S2
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
Canonical SMILES: C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
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
InChIKey: YPZRWBKMTBYPTK-BJDJZHNGSA-N

Cross-matching ID

PubChem CID: 65359
ChEBI ID: CHEBI:17858
CAS Number: 27025-41-8
UNII: ULW86O013H
DrugBank ID: DB03310
TTD ID: D0V4TY

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Glutathione reductase (GR)	TTEP6RV	GSHR_HUMAN	Inhibitor	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Alpha-synuclein (SNCA)	OTPWC1MR	SYUA_HUMAN	Regulation of Drug Effects	[4]
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Protein Interaction/Cellular Processes	[5]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Post-Translational Modifications	[6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[7]
Cystic fibrosis transmembrane conductance regulator (CFTR)	OT6B22QH	CFTR_HUMAN	Gene/Protein Processing	[8]
Gamma-crystallin D (CRYGD)	OTW29JC4	CRGD_HUMAN	Post-Translational Modifications	[9]
Multidrug resistance-associated protein 1 (ABCC1)	OTGUN89S	MRP1_HUMAN	Regulation of Drug Effects	[10]
Nicotinamide N-methyltransferase (NNMT)	OTFM38GU	NNMT_HUMAN	Regulation of Drug Effects	[11]
Superoxide dismutase , mitochondrial (SOD2)	OTIWXGZ9	SODM_HUMAN	Regulation of Drug Effects	[12]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	D-Ala-D-Ala ligases from glycopeptide antibiotic-producing organisms are highly homologous to the enterococcal vancomycin-resistance ligases VanA and VanB. Proc Natl Acad Sci U S A. 1997 Jun 10;94(12):6480-3.
3	The purification and properties of glutathione reductase from the cestode Moniezia expansa. Int J Biochem Cell Biol. 1995 Apr;27(4):393-401.
4	Alpha-synuclein-induced oxidative stress correlates with altered superoxide dismutase and glutathione synthesis in human neuroblastoma SH-SY5Y cells. Arch Toxicol. 2017 Mar;91(3):1245-1259.
5	Identifying environmental chemicals as agonists of the androgen receptor by using a quantitative high-throughput screening platform. Toxicology. 2017 Jun 15;385:48-58. doi: 10.1016/j.tox.2017.05.001. Epub 2017 May 4.
6	Human p53 is inhibited by glutathionylation of cysteines present in the proximal DNA-binding domain during oxidative stress. Biochemistry. 2007 Jul 3;46(26):7765-80. doi: 10.1021/bi700425y. Epub 2007 Jun 8.
7	Activation of c-Jun-N-terminal kinase is required for apoptosis triggered by glutathione disulfide in neuroblastoma cells. Free Radic Biol Med. 2005 Aug 1;39(3):345-54. doi: 10.1016/j.freeradbiomed.2005.03.022. Epub 2005 Apr 7.
8	Reversible silencing of CFTR chloride channels by glutathionylation. J Gen Physiol. 2005 Feb;125(2):127-41. doi: 10.1085/jgp.200409115. Epub 2005 Jan 18.
9	Dynamic disulfide exchange in a crystallin protein in the human eye lens promotes cataract-associated aggregation. J Biol Chem. 2018 Nov 16;293(46):17997-18009. doi: 10.1074/jbc.RA118.004551. Epub 2018 Sep 21.
10	Role of the multidrug resistance protein-1 in hypertension and vascular dysfunction caused by angiotensin II. Arterioscler Thromb Vasc Biol. 2007 Apr;27(4):762-8. doi: 10.1161/01.ATV.0000259298.11129.a2. Epub 2007 Feb 1.
11	Nicotinamide N-methyltransferase expression in SH-SY5Y human neuroblastoma cells decreases oxidative stress. J Biochem Mol Toxicol. 2020 Mar;34(3):e22439. doi: 10.1002/jbt.22439. Epub 2020 Jan 7.
12	Alteration of cellular phenotype and responses to oxidative stress by manganese superoxide dismutase and a superoxide dismutase mimic in RWPE-2 human prostate adenocarcinoma cells. Antioxid Redox Signal. 2004 Jun;6(3):513-22. doi: 10.1089/152308604773934279.