Details of the Drug

General Information of Drug (ID: DMZ9WI4)

• Drug Name: Nitrosoglutathione
• Synonyms: Glutathione thionitrite; Nitrosoglutathione; S-nitrosoglutathione; S-NITROSO-L-GLUTATHIONE; (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid; (S)-2-Amino-5-(((R)-1-((carboxymethyl)amino)-3-(nitrosothio)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid; 57564-91-7; 78RRI89ZTO; BRN 3566211; C10H16N4O7S; CCRIS 2095; CHEBI:50091; Glycine, N-(N-L-gamma-glutamyl-S-nitroso-L-cysteinyl)-; N-(N-L-gamma-Glutamyl-S-nitroso-L-cysteinyl)glycine; SNOG; UNII-78RRI89ZTO; gsno
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 336.32
  Logarithm of the Partition Coefficient (xlogp); -4.8
  Rotatable Bond Count (rotbonds); 10
  Hydrogen Bond Donor Count (hbonddonor); 5
  Hydrogen Bond Acceptor Count (hbondacc); 10
• Chemical Identifiers:
  Formula: C10H16N4O7S
  IUPAC Name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
  Canonical SMILES: C(CC(=O)NC(CSN=O)C(=O)NCC(=O)O)C(C(=O)O)N
  InChI: HYHSBSXUHZOYLX-WDSKDSINSA-N
  InChIKey: 1S/C10H16N4O7S/c11-5(10(19)20)1-2-7(15)13-6(4-22-14-21)9(18)12-3-8(16)17/h5-6H,1-4,11H2,(H,12,18)(H,13,15)(H,16,17)(H,19,20)/t5-,6-/m0/s1
• Cross-matching ID:
  PubChem CID: 104858
  ChEBI ID: CHEBI:50091
  CAS Number: 57564-91-7
  INTEDE ID: DR2448

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
S-(hydroxymethyl)glutathione dehydrogenase (adh) Main DME	DEAH3PE	A0A0A7DS01_VIBCL	Substrate	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Alcohol dehydrogenase class-3 (ADH5)	OTSO67MI	ADHX_HUMAN	Biotransformations	[2]
C-C motif chemokine 5 (CCL5)	OTSCA5CK	CCL5_HUMAN	Protein Interaction/Cellular Processes	[3]
C-X-C motif chemokine 10 (CXCL10)	OTTLQ6S0	CXL10_HUMAN	Protein Interaction/Cellular Processes	[3]
Carbonyl reductase 1 (CBR1)	OTQ3A541	CBR1_HUMAN	Biotransformations	[4]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[5]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[5]
Cystic fibrosis transmembrane conductance regulator (CFTR)	OT6B22QH	CFTR_HUMAN	Gene/Protein Processing	[6]
Heme oxygenase 1 (HMOX1)	OTC1W6UX	HMOX1_HUMAN	Gene/Protein Processing	[7]
Hypoxia-inducible factor 1-alpha (HIF1A)	OTADSC03	HIF1A_HUMAN	Gene/Protein Processing	[8]
Interferon gamma (IFNG)	OTXG9JM7	IFNG_HUMAN	Protein Interaction/Cellular Processes	[3]

References

• [1] Nitrosative stress response in Vibrio cholerae: role of S-nitrosoglutathione reductase. Appl Biochem Biotechnol. 2017 Jul;182(3):871-884.
• [2] The Janus face of alcohol dehydrogenase 3. Chem Biol Interact. 2009 Mar 16;178(1-3):29-35. doi: 10.1016/j.cbi.2008.10.050. Epub 2008 Nov 6.
• [3] Regulatory role of nitric oxide on monocyte-derived dendritic cell functions. J Interferon Cytokine Res. 2003 Aug;23(8):423-31. doi: 10.1089/107999003322277838.
• [4] Studies on reduction of S-nitrosoglutathione by human carbonyl reductases 1 and 3. Chem Biol Interact. 2011 May 30;191(1-3):95-103.
• [5] The induction of reactive oxygen species and loss of mitochondrial Omi/HtrA2 is associated with S-nitrosoglutathione-induced apoptosis in human endothelial cells. Toxicol Appl Pharmacol. 2010 May 1;244(3):374-84. doi: 10.1016/j.taap.2010.02.004. Epub 2010 Feb 11.
• [6] Concentration-dependent effects of endogenous S-nitrosoglutathione on gene regulation by specificity proteins Sp3 and Sp1. Biochem J. 2004 May 15;380(Pt 1):67-74. doi: 10.1042/BJ20031687.
• [7] Induction of heme oxygenase-1 as a response in sensing the signals evoked by distinct nitric oxide donors. Biochem Pharmacol. 1999 Jul 15;58(2):227-36. doi: 10.1016/s0006-2952(99)00097-0.
• [8] Regulation of the hypoxia-inducible factor 1alpha by the inflammatory mediators nitric oxide and tumor necrosis factor-alpha in contrast to desferroxamine and phenylarsine oxide. J Biol Chem. 2001 Oct 26;276(43):39805-11. doi: 10.1074/jbc.M107689200. Epub 2001 Aug 20.