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Details

Stereochemistry ABSOLUTE
Molecular Formula C3H7NO3S
Molecular Weight 137.158
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYSTEINESULFENIC ACID

SMILES

N[C@@H](CSO)C(O)=O

InChI

InChIKey=FXIRVRPOOYSARH-REOHCLBHSA-N
InChI=1S/C3H7NO3S/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

HIDE SMILES / InChI

Molecular Formula C3H7NO3S
Molecular Weight 137.158
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Structural analysis of actinidin and a comparison of cadmium and sulfur anomalous signals from actinidin crystals measured using in-house copper- and chromium-anode X-ray sources.
2010-12
Cysteine sulfenic acid as an intermediate in disulfide bond formation and nonenzymatic protein folding.
2010-09-07
Formation of cysteine sulfenic acid by oxygen atom transfer from nitrite.
2010-07-14
Possibilities and pitfalls in quantifying the extent of cysteine sulfenic acid modification of specific proteins within complex biofluids.
2010-07-01
Regulation of redox signaling by selenoproteins.
2010-06
Kinetic and structural studies on roles of the serine ligand and a strictly conserved tyrosine residue in nitrile hydratase.
2010-06
Extracellular SOD-derived H2O2 promotes VEGF signaling in caveolae/lipid rafts and post-ischemic angiogenesis in mice.
2010-04-21
Discovery of fragment molecules that bind the human peroxiredoxin 5 active site.
2010-03-17
Effects of MMP-9 inhibition by doxycycline on proteome of lungs in high tidal volume mechanical ventilation-induced acute lung injury.
2010-01-29
"Danger" conditions increase sulfamethoxazole-protein adduct formation in human antigen-presenting cells.
2009-11
Structural basis for catalytic activation of thiocyanate hydrolase involving metal-ligated cysteine modification.
2009-10-21
Hemoglobin glutathionylation can occur through cysteine sulfenic acid intermediate: electrospray ionization LTQ-Orbitrap hybrid mass spectrometry studies.
2009-10-15
Characterization of a salt-induced DhAHP, a gene coding for alkyl hydroperoxide reductase, from the extremely halophilic yeast Debaryomyces hansenii.
2009-08-28
Characterization of novel oxidation products of cysteine in an active site motif peptide of PTP1B.
2009-08
Chemical dissection of an essential redox switch in yeast.
2009-02-27
Structures of the multicomponent Rieske non-heme iron toluene 2,3-dioxygenase enzyme system.
2009-01
Cysteine pK(a) values for the bacterial peroxiredoxin AhpC.
2008-12-02
Structural characterization and reversal of the natural organophosphate resistance of a D-type esterase, Saccharomyces cerevisiae S-formylglutathione hydrolase.
2008-09-09
Function and structure of a prokaryotic formylglycine-generating enzyme.
2008-07-18
Role of glutaredoxin 2 and cytosolic thioredoxins in cysteinyl-based redox modification of the 20S proteasome.
2008-06
Peroxiredoxin 6 in human brain: molecular forms, cellular distribution and association with Alzheimer's disease pathology.
2008-06
Reactive sulfur species: kinetics and mechanism of the equilibrium between cysteine sulfenyl thiocyanate and cysteine thiosulfinate ester in acidic aqueous solution.
2008-04-18
A novel OxyR sensor and regulator of hydrogen peroxide stress with one cysteine residue in Deinococcus radiodurans.
2008-02-13
Functional site profiling and electrostatic analysis of cysteines modifiable to cysteine sulfenic acid.
2008-02
Redox regulation and trapping sulfenic acid in the peroxide-sensitive human mitochondrial branched chain aminotransferase.
2008
Thiourea-enhanced flavin photooxidation of benzyl alcohol.
2008
A genetically encoded probe for cysteine sulfenic acid protein modification in vivo.
2007-12-18
Fluorescent and affinity-based tools to detect cysteine sulfenic acid formation in proteins.
2007-11-23
The requirement of reversible cysteine sulfenic acid formation for T cell activation and function.
2007-11-15
Reactive sulfur species: kinetics and mechanisms of the oxidation of cysteine by hypohalous acid to give cysteine sulfenic acid.
2007-11-14
Reactive sulfur species: kinetics and mechanisms of the reaction of cysteine thiosulfinate ester with cysteine to give cysteine sulfenic acid.
2007-11-09
Molecular mechanism of oxidative stress perception by the Orp1 protein.
2007-10-26
Characterization by tandem mass spectrometry of stable cysteine sulfenic acid in a cysteine switch peptide of matrix metalloproteinases.
2007-08
Evolution of function in the "two dinucleotide binding domains" flavoproteins.
2007-07
The catalytic mechanism of peroxiredoxins.
2007
How does single oxygen atom addition affect the properties of an Fe-nitrile hydratase analogue? The compensatory role of the unmodified thiolate.
2006-08-30
Molecular basis for multiple sulfatase deficiency and mechanism for formylglycine generation of the human formylglycine-generating enzyme.
2005-05-20
Bacterial defenses against oxidants: mechanistic features of cysteine-based peroxidases and their flavoprotein reductases.
2005-01-01
Flavoprotein disulfide reductases: advances in chemistry and function.
2004
Molecular characterization of NikD, a new flavoenzyme important in the biosynthesis of nikkomycin antibiotics.
2002-12-31
Identification of cysteine sulfenic acid in AhpC of alkyl hydroperoxide reductase.
2002
Oxidation of active center cysteine of bovine 1-Cys peroxiredoxin to the cysteine sulfenic acid form by peroxide and peroxynitrite.
2001-08-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:29:14 GMT 2025
Edited
by admin
on Mon Mar 31 19:29:14 GMT 2025
Record UNII
FB8KIA847T
Record Status Validated (UNII)
Record Version
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Name Type Language
CYSTEINESULFENIC ACID
Common Name English
CYSTEINE SULFENIC ACID
Preferred Name English
S-HYDROXYCYSTEINE
Systematic Name English
L-CYSTEINE SULFOXIDE
Common Name English
L-ALANINE, 3-SULFENO-
Systematic Name English
L-CYSTEINESULFENIC ACID
Common Name English
Code System Code Type Description
CHEBI
41630
Created by admin on Mon Mar 31 19:29:14 GMT 2025 , Edited by admin on Mon Mar 31 19:29:14 GMT 2025
PRIMARY
FDA UNII
FB8KIA847T
Created by admin on Mon Mar 31 19:29:14 GMT 2025 , Edited by admin on Mon Mar 31 19:29:14 GMT 2025
PRIMARY
DRUG BANK
DB01915
Created by admin on Mon Mar 31 19:29:14 GMT 2025 , Edited by admin on Mon Mar 31 19:29:14 GMT 2025
PRIMARY
CHEBI
41710
Created by admin on Mon Mar 31 19:29:14 GMT 2025 , Edited by admin on Mon Mar 31 19:29:14 GMT 2025
PRIMARY
PUBCHEM
165339
Created by admin on Mon Mar 31 19:29:14 GMT 2025 , Edited by admin on Mon Mar 31 19:29:14 GMT 2025
PRIMARY
CAS
73243-12-6
Created by admin on Mon Mar 31 19:29:14 GMT 2025 , Edited by admin on Mon Mar 31 19:29:14 GMT 2025
PRIMARY