| InChI=1S/HNOS/c2-1-3/h(H,2,3) |
| ICRHORQIUXBEPA-UHFFFAOYSA-N |
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via hydracid )
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signalling molecule
A molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell.
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View more via ChEBI Ontology
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(hydridosulfanido)oxidonitrogen
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IUPAC
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HSN=O
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ChEBI
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HSNO
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ChEBI
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nitrosomercaptan
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ChEBI
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nitrosothiol
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ChEBI
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S-nitrosothiol
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ChEBI
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13564781
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Reaxys Registry Number
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Reaxys
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Filipovic MR, Miljkovic JLj, Nauser T, Royzen M, Klos K, Shubina T, Koppenol WH, Lippard SJ, Ivanović-Burmazović I (2012)
Chemical characterization of the smallest S-nitrosothiol, HSNO; cellular cross-talk of H2S and S-nitrosothiols.
Journal of the American Chemical Society 134, 12016-12027 [PubMed:22741609]
[show Abstract]
Dihydrogen sulfide recently emerged as a biological signaling molecule with important physiological roles and significant pharmacological potential. Chemically plausible explanations for its mechanisms of action have remained elusive, however. Here, we report that H(2)S reacts with S-nitrosothiols to form thionitrous acid (HSNO), the smallest S-nitrosothiol. These results demonstrate that, at the cellular level, HSNO can be metabolized to afford NO(+), NO, and NO(-) species, all of which have distinct physiological consequences of their own. We further show that HSNO can freely diffuse through membranes, facilitating transnitrosation of proteins such as hemoglobin. The data presented in this study explain some of the physiological effects ascribed to H(2)S, but, more broadly, introduce a new signaling molecule, HSNO, and suggest that it may play a key role in cellular redox regulation. | Timerghazin QK, Peslherbe GH, English AM (2008)
Structure and stability of HSNO, the simplest S-nitrosothiol.
Physical chemistry chemical physics : PCCP 10, 1532-1539 [PubMed:18327309]
[show Abstract]
High-level ab initio calculations employing the CCSD and CCSD(T) coupled cluster methods with a series of systematically convergent correlation-consistent basis sets have been performed to obtain accurate molecular geometry and energetic properties of the simplest S-nitrosothiol (RSNO), HSNO. The properties of the S-N bond, which are central to the physiological role of RSNOs in the storage and transport of nitric oxide, are highlighted. Following corrections for quadruple excitations, core-valence correlation and relativistic effects, the CCSD(T) method extrapolated to the complete basis set (CBS) limit yielded values of 1.85 A and 29.2 kcal mol(-1) for the S-N bond length and the dissociation energy for homolysis of the S-N bond, respectively, in the energetically most stable trans-conformer of HSNO. The properties of the S-N bond strongly depend on the basis-set size and the inclusion of triple, and, to a lesser extent, quadruple excitations in the coupled cluster expansion. CCSD calculations systematically underestimate the S-N equilibrium distance and S-N bond dissociation energy by 0.05-0.07 A and 6-7 kcal mol(-1), respectively. The significant differences between the CCSD(T) and CCSD descriptions of HSNO, the high values of the coupled cluster T(1) (0.027) and D(1) (0.076) diagnostics, as well as the instability of the reference restricted Hartree-Fock (RHF) wavefunction indicate that the electronic structure of the SNO group possesses multireference character. Previous quantum-chemical data on RSNOs are reexamined based on the new insight into the SNO electronic structure obtained from the present high-level calculations on HSNO. |
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