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Showing Compound S-Nitrosoglutathione (FDB023390)

Record Information
Version1.0
Creation date2011-09-21 00:29:14 UTC
Update date2015-07-21 06:57:41 UTC
Primary IDFDB023390
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-Nitrosoglutathione
DescriptionS-Nitrosoglutathione is a S-nitrosothiol. S-nitrosothiols (RSNOs) are thought to represent a circulating endogenous reservoir of nitric oxide (NO), and may have potential as donors of nitric oxide, distinct from currently used agents. They have the general formula RSNO, and naturally occurring examples include S-nitrosocysteine, S-nitrosoglutathione and S-nitrosoalbumin, in which R is an amino acid, polypeptide and protein respectively. RSNOs have anti-platelet properties, a theoretical role in the treatment of asthma and the potential to be used as agents to treat infectious diseases ranging from the common cold to AIDS. RSNOs are relatively unstable, being degraded to release nitric oxide and the corresponding disulphide. Their stability is influenced by the properties of the R group, heat, light, the presence of transition metal ions (in particular copper) and the presence of other thiols. RSNOs participate in transnitrosation reactions in which the -nitric oxide group is transferred to another thiol to form a more stable RSNO. Potential interactions of RSNOs include that with ascorbic acid (vitamin C), which enhances the ability of copper to catalyse their degradation. Transnitrosation reactions with thiol-containing enzymes can influence protein function, and the intracellular thiol glutathione, levels of which are influenced by many disease states, can also influence stability. Genetic and biochemical data demonstrate a pivotal role for S-nitrosothiols in mediating the actions of nitric oxide synthases (NOSs). RSNOs serve to convey NO bioactivity and to regulate protein function. S-Nitrosoglutathione breakdown is subject to precise regulation. For example, S-Nitrosoglutathione reductase (GSNOR) breaks down cytosolic S-Nitrosoglutathione, ultimately to oxidized GSH and ammonia. GSNOR, in turn, modulates the levels of some S-nitrosylated proteins. S-nitrosoglutathione, formed as nitric oxide moves away from erythrocytes in response to hemoglobin desaturation, may signal hypoxia-inducible factor-1-mediated physiologic and gene regulatory events in pulmonary endothelial cells without profound hypoxia, through a thiol-based reaction. S-Nitrosoglutathione stabilizes the alpha-subunit of hypoxia inducible factor1 (HIF-1) in normoxic cells, but not in the presence of PI3K inhibitors. (PMID: 11749666, 17541013, 16528016) [HMDB]
CAS Number57564-91-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.73 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.6ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area188.25 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity74.48 m³·mol⁻¹ChemAxon
Polarizability30.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16N4O7S
IUPAC name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid
InChI IdentifierInChI=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
InChI KeyHYHSBSXUHZOYLX-WDSKDSINSA-N
Isomeric SMILESN[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O)C(O)=O
Average Molecular Weight336.322
Monoisotopic Molecular Weight336.073969576
Classification
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Organic s-nitroso compound
  • Amino acid or derivatives
  • Amino acid
  • Nitrosothiol
  • Nitrosothiol-group
  • Organic nitroso compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-Nitrosoglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7492000000-b8047614ec6fd11afa64Spectrum
Predicted GC-MSS-Nitrosoglutathione, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00rl-9221500000-4b61aaeb02d9e9a1ce8fSpectrum
Predicted GC-MSS-Nitrosoglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-Nitrosoglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mx-2195000000-a563223d38cc871e075e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-5690000000-602911e49e2773fc604a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6910000000-ec94284144a3d795c0582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-1069000000-64cab5a8bb487605b5dd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07p0-5494000000-a77a2e8025c498cc7bd42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022c-9400000000-3a9e24cebbb82d680c462017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0139000000-a465a5f3cb9aeab179612021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0961000000-b3a2bbbe2a8374ddba482021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9700000000-7c8a8435959ceff23bf02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fe0-0469000000-67ad5cd47cd93ab5f9652021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9721000000-069b0ee7c891f9f284692021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9400000000-5343c1d557eb50ff2bb52021-09-22View Spectrum
NMRNot Available
ChemSpider ID94647
ChEMBL IDCHEMBL63507
KEGG Compound IDNot Available
Pubchem Compound ID104858
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04645
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference