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38520-57-9 | (R)-2-Acetamido-3-mercaptopropanamide
CAS No: 38520-57-9 Catalog No: AG00368B MDL No:MFCD01696115
Product Description
Catalog Number:
AG00368B
Chemical Name:
(R)-2-Acetamido-3-mercaptopropanamide
CAS Number:
38520-57-9
Molecular Formula:
C5H10N2O2S
Molecular Weight:
162.2101
MDL Number:
MFCD01696115
IUPAC Name:
(2R)-2-acetamido-3-sulfanylpropanamide
InChI:
InChI=1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1
InChI Key:
UJCHIZDEQZMODR-BYPYZUCNSA-N
SMILES:
SC[C@@H](C(=O)N)NC(=O)C
UNII:
4N69717RKW
Properties
Complexity:
149
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
162.046g/mol
Formal Charge:
0
Heavy Atom Count:
10
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
162.207g/mol
Monoisotopic Mass:
162.046g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
73.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3
Literature
| Title | Journal |
|---|---|
| N-acetylcysteine amide, a promising antidote for acetaminophen toxicity. | Toxicology letters 20160122 |
| Estrogen Sulfotransferase Is an Oxidative Stress-responsive Gene That Gender-specifically Affects Liver Ischemia/Reperfusion Injury. | The Journal of biological chemistry 20150605 |
| N-acetylcysteine amide protects against methamphetamine-induced tissue damage in CD-1 mice. | Human & experimental toxicology 20120901 |
| Characterizing N-acetylcysteine (NAC) and N-acetylcysteine amide (NACA) binding for lead poisoning treatment. | Journal of colloid and interface science 20120401 |
| Mutations in the mitochondrial methionyl-tRNA synthetase cause a neurodegenerative phenotype in flies and a recessive ataxia (ARSAL) in humans. | PLoS biology 20120301 |
| Blood-brain barrier abnormalities caused by HIV-1 gp120: mechanistic and therapeutic implications. | TheScientificWorldJournal 20120101 |
| Protective effects of N-acetylcysteine amide (NACA) on gentamicin-induced apoptosis in LLC-PK1 cells. | Renal failure 20120101 |
| Glutathione homeostasis and functions: potential targets for medical interventions. | Journal of amino acids 20120101 |
| Free radical scavenger properties of α-mangostin: thermodynamics and kinetics of HAT and RAF mechanisms. | The journal of physical chemistry. B 20111103 |
| Effectiveness of sulfur-containing antioxidants in delaying skeletal muscle fatigue. | Medicine and science in sports and exercise 20110601 |
| Directing dopaminergic fiber growth along a preformed molecular pathway from embryonic ventral mesencephalon transplants in the rat brain. | Journal of neuroscience research 20110501 |
| N-acetylcysteine amide (NACA) prevents retinal degeneration by up-regulating reduced glutathione production and reversing lipid peroxidation. | The American journal of pathology 20110501 |
| Highly active antiretroviral therapy drug combination induces oxidative stress and mitochondrial dysfunction in immortalized human blood-brain barrier endothelial cells. | Free radical biology & medicine 20110401 |
| In vivo inhibition of l-buthionine-(S,R)-sulfoximine-induced cataracts by a novel antioxidant, N-acetylcysteine amide. | Free radical biology & medicine 20110315 |
| Comparative evaluation of N-acetylcysteine (NAC) and N-acetylcysteine amide (NACA) on glutamate and lead-induced toxicity in CD-1 mice. | Toxicology letters 20110225 |
| Hypoxia-inducible factor-1 α/platelet derived growth factor axis in HIV-associated pulmonary vascular remodeling. | Respiratory research 20110101 |
| In vitro acute exposure to DEHP affects oocyte meiotic maturation, energy and oxidative stress parameters in a large animal model. | PloS one 20110101 |
| The HIV-1 transactivator factor (Tat) induces enterocyte apoptosis through a redox-mediated mechanism. | PloS one 20110101 |
| Effects of N-acetyl-cysteine and N-acetyl-cysteine-amide supplementation on in vitro matured porcine oocytes. | Reproduction in domestic animals = Zuchthygiene 20101001 |
| HIV proteins (gp120 and Tat) and methamphetamine in oxidative stress-induced damage in the brain: potential role of the thiol antioxidant N-acetylcysteine amide. | Free radical biology & medicine 20100515 |
| N-acetylcysteine amide protects renal proximal tubular epithelial cells against iohexol-induced apoptosis by blocking p38 MAPK and iNOS signaling. | American journal of nephrology 20100101 |
| Attenuation of pulmonary inflammation after exposure to blast overpressure by N-acetylcysteine amide. | Shock (Augusta, Ga.) 20090901 |
| N-acetylcysteineamide (NACA) prevents inflammation and oxidative stress in animals exposed to diesel engine exhaust. | Toxicology letters 20090622 |
| N-Acetylcysteine amide protects against methamphetamine-induced oxidative stress and neurotoxicity in immortalized human brain endothelial cells. | Brain research 20090612 |
| N-acetylcysteine amide decreases oxidative stress but not cell death induced by doxorubicin in H9c2 cardiomyocytes. | BMC pharmacology 20090101 |
| Anti-inflammatory and arthritic effects of thiacremonone, a novel sulfur compound isolated from garlic via inhibition of NF-kappaB. | Arthritis research & therapy 20090101 |
| Effects of N-acetylcysteine amide (NACA), a thiol antioxidant on radiation-induced cytotoxicity in Chinese hamster ovary cells. | Life sciences 20080523 |
| Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC). | Free radical research 20080401 |
| N-acetylcysteine amide (AD4) attenuates oxidative stress in beta-thalassemia blood cells. | Biochimica et biophysica acta 20080201 |
| Endoplasmic reticulum stress and unfolded protein response in Atm-deficient thymocytes and thymic lymphoma cells are attributable to oxidative stress. | Neoplasia (New York, N.Y.) 20080201 |
| A novel thiol compound, N-acetylcysteine amide, attenuates allergic airway disease by regulating activation of NF-kappaB and hypoxia-inducible factor-1alpha. | Experimental & molecular medicine 20071231 |
| [N-acetylcysteine improves lysosomal function and enhances the degradation of photoreceptor outer segments in cultured RPE cells]. | Klinische Monatsblatter fur Augenheilkunde 20070701 |
| Advanced glycation end products attenuate cellular insulin sensitivity by increasing the generation of intracellular reactive oxygen species in adipocytes. | Diabetes research and clinical practice 20070501 |
| Role of N-acetylcysteine in the management of COPD. | International journal of chronic obstructive pulmonary disease 20061201 |
| Potentiation of lead-induced cell death in PC12 cells by glutamate: protection by N-acetylcysteine amide (NACA), a novel thiol antioxidant. | Toxicology and applied pharmacology 20061015 |
| A novel antioxidant N-acetylcysteine amide prevents gp120- and Tat-induced oxidative stress in brain endothelial cells. | Experimental neurology 20060901 |
| Separation and quantification of N-acetyl-l-cysteine and N-acetyl-cysteine-amide by HPLC with fluorescence detection. | Biomedical chromatography : BMC 20060501 |
| Low molecular weight thiol amides attenuate MAPK activity and protect primary neurons from Abeta(1-42) toxicity. | Brain research 20060119 |
| Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12. | Brain research 20050921 |
| Is brain dehydroepiandrosterone synthesis modulated by free radicals in mice? | Neuroscience letters 20050329 |
| N-acetylcysteine amide, a novel cell-permeating thiol, restores cellular glutathione and protects human red blood cells from oxidative stress. | Free radical biology & medicine 20050101 |
| Analysis of gene expression in MOG-induced experimental autoimmune encephalomyelitis after treatment with a novel brain-penetrating antioxidant. | Journal of molecular neuroscience : MN 20050101 |
| A novel brain-targeted antioxidant (AD4) attenuates haloperidol-induced abnormal movement in rats: implications for tardive dyskinesia. | Clinical neuropharmacology 20050101 |
| A low molecular weight copper chelator crosses the blood-brain barrier and attenuates experimental autoimmune encephalomyelitis. | Journal of neurochemistry 20040601 |
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