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S-Nitroso-N-acetylpenicillamine

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S-Nitroso-N-acetylpenicillamine
Skeletal formula of SNAP
Ball-and-stick model of SNAP
Names
IUPAC name S-Nitroso-N-acetylpenicillamine
Other names N-Acetyl-3-(nitrosothio)-DL-valine
S-Nitroso-N-acetylpenicillamine
Identifiers
CAS Number
3D model (JSmol)
Abbreviations SNAP
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)/t5-/m0/s1Key: ZIIQCSMRQKCOCT-YFKPBYRVSA-N
  • InChI=1/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)/t5-/m0/s1Key: ZIIQCSMRQKCOCT-YFKPBYRVBE
SMILES
  • O=C(N(C(=O)O)C(SN=O)(C)C)C
Properties
Chemical formula C7H12N2O4S
Molar mass 220.25 g/mol
Appearance green solid
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

S-Nitroso-N-acetylpenicillamine (SNAP) is the organosulfur compound with the formula ONSC(CH3)2CH(NHAc)CO2H. It is a green solid.

SNAP is an S-nitrosothiol and is used as a model for the general class of S-nitrosothiols which have received much attention in biochemistry because nitric oxide and some organic nitroso derivatives serve as signaling molecules in living systems, especially related to vasodilation. SNAP is derived from the amino acid penicillamine. S-Nitrosoglutathione is a related agent.

References

  1. "N3398 h S-Nitroso-N-acetyl-DL-penicillamine". Sigma-Aldric. Retrieved 13 December 2021.
  2. Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. (1999). "Interrelationships between Conformational Dynamics and the Redox Chemistry of S-Nitrosothiols". Journal of the American Chemical Society. 121 (30): 7115–7123. doi:10.1021/ja9901314.
  3. Zhang Y.; Hogg, N. (2005). "S-Nitrosothiols: Cellular Formation and Transport". Free Radical Biology and Medicine. 38 (7): 831–838. doi:10.1016/j.freeradbiomed.2004.12.016. PMID 15749378.
Nitric oxide signaling modulators
Forms
Targets
sGC
  • Inhibitors: ODQ
NO donors
(prodrugs)
Enzyme
(inhibitors)
NOS
nNOS
iNOS
eNOS
Unsorted
Arginase
CAMK
Others
See also: Receptor/signaling modulators
Categories: