Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C6H12N2O4S2 |
| Molecular Weight | 240.3 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@H](CSSC[C@@H](N)C(O)=O)C(O)=O
InChI
InChIKey=LEVWYRKDKASIDU-QWWZWVQMSA-N
InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m1/s1
| Molecular Formula | C6H12N2O4S2 |
| Molecular Weight | 240.3 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7173742 | https://www.ncbi.nlm.nih.gov/pubmed/11709062 | https://www.drugbank.ca/drugs/DB00138
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7173742 | https://www.ncbi.nlm.nih.gov/pubmed/11709062 | https://www.drugbank.ca/drugs/DB00138
DL-Cystine is a racemic mixture of the proteinogenic amino acids L-cystine and the non-proteinogenic D-cystine. Cystine is the oxidized dimer form of the amino acid cysteine. L-Cystine serves two biological functions, a site of redox reactions and a mechanical linkage that allows proteins to retain their 3-dimensional structure. DL-cystine is used in the preparation of sulfur-containing dimeric and monomeric surfactants.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Epidermal proteins of cultured human and bovine keratinocytes. | 1979 Jun 19 |
|
| The cystine-rich envelope protein from human epidermal stratum corneum cells. | 1987 Jan |
|
| Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. | 1991 Jan 2 |
|
| Modulation of glutathione S-transferase activity by a thiol/disulfide exchange reaction and involvement of thioltransferase. | 1993 Jan |
|
| Synthesis and metabolism of oxytocin in late gestation in human decidua. | 1995 |
|
| Targeting of liver metastases of colorectal cancer with IgG, F(ab')2, and Fab' anti-carcinoembryonic antigen antibodies labeled with 99mTc: the role of metabolism and kinetics. | 1995 Dec 1 |
|
| Pathogenesis and medical management of cystinuria. | 1996 Sep |
|
| [Leber's hereditary optic neuropathy]. | 2001 Mar-Apr |
|
| Probing conformational changes in the I-like domain and the cysteine-rich repeat of human beta 3 integrins following disulfide bond disruption by cysteine mutations: identification of cysteine 598 involved in alphaIIbbeta3 activation. | 2001 Oct 19 |
|
| Pediatric urolithiasis in Armenia: a study of 198 patients observed from 1991 to 1999. | 2001 Sep |
|
| Tetraethylammonium block of water flux in Aquaporin-1 channels expressed in kidney thin limbs of Henle's loop and a kidney-derived cell line. | 2002 |
|
| Complete structure of an increasing capillary permeability protein (ICPP) purified from Vipera lebetina venom. ICPP is angiogenic via vascular endothelial growth factor receptor signalling. | 2002 Aug 16 |
|
| The consequences of methylmercury exposure on interactive functions between astrocytes and neurons. | 2002 Dec |
|
| Lysosomal cystine storage augments apoptosis in cultured human fibroblasts and renal tubular epithelial cells. | 2002 Dec |
|
| Trans-differentiation of prostatic stromal cells leads to decreased glycoprotein hormone alpha production. | 2002 Nov |
|
| Electrophile response element-mediated induction of the cystine/glutamate exchange transporter gene expression. | 2002 Nov 22 |
|
| A mouse model for cystinuria type I. | 2003 Sep 1 |
|
| Modification of cysteine residue in transthyretin and a synthetic peptide: analyses by electrospray ionization mass spectrometry. | 2004 Apr 8 |
|
| Screening for biochemical abnormalities in urolithiasis patients. | 2004 Apr-Jun |
|
| Plasma and cerebrospinal fluid amino acids in epileptic patients. | 2004 Jan |
|
| Properties and significance of apoFNR as a second form of air-inactivated [4Fe-4S].FNR of Escherichia coli. | 2005 Aug |
|
| Cystinosis as a cause of noncirrhotic portal hypertension. | 2005 Jul |
|
| Mechanism of the conversion of xanthine dehydrogenase to xanthine oxidase: identification of the two cysteine disulfide bonds and crystal structure of a non-convertible rat liver xanthine dehydrogenase mutant. | 2005 Jul 1 |
|
| A strategy using NMR peptide structures of thromboxane A2 receptor as templates to construct ligand-recognition pocket of prostacyclin receptor. | 2005 Nov 4 |
|
| Kidney stone disease. | 2005 Oct |
|
| Evaluation of commercial kits for the identification of Neisseria gonorrhoeae. | 2005 Sep |
|
| Changing cellular location of CheZ predicted by molecular simulations. | 2006 Apr |
|
| Mechanistic implications of the structure of the mixed-disulfide intermediate of the disulfide oxidoreductase, 2-ketopropyl-coenzyme M oxidoreductase/carboxylase. | 2006 Jan 10 |
|
| High-level production of bioactive human beta-defensin-4 in Escherichia coli by soluble fusion expression. | 2006 Sep |
|
| Structural and Functional Determinants of gamma-Secretase, an Intramembrane Protease Implicated in Alzheimer's Disease. | 2007 Dec |
|
| Detailed structural analysis of amyloidogenic wild-type transthyretin using a novel purification strategy and mass spectrometry. | 2007 Mar 1 |
|
| A bacterial two-hybrid system based on the twin-arginine transporter pathway of E. coli. | 2007 May |
|
| Structure and conformation of the disulfide bond in dimeric lung surfactant peptides SP-B1-25 and SP-B8-25. | 2007 May |
|
| Left handed beta helix models for mammalian prion fibrils. | 2008 Apr-Jun |
|
| Mutation in the cysteine bridge domain of the gamma-subunit affects light regulation of the ATP synthase but not photosynthesis or growth in Arabidopsis. | 2008 Aug |
|
| High-level expression and novel purification strategy of recombinant thanatin analog in Escherichia coli. | 2008 Aug |
|
| Production of bioactive human beta-defensin 5 and 6 in Escherichia coli by soluble fusion expression. | 2008 Oct |
|
| Molecular characterization and complete genome sequence of avian paramyxovirus type 4 prototype strain duck/Hong Kong/D3/75. | 2008 Oct 20 |
|
| Intestinal barrier function in response to abundant or depleted mucosal glutathione in Salmonella-infected rats. | 2009 Apr 17 |
|
| Oxidation of bovine serum albumin: identification of oxidation products and structural modifications. | 2009 Aug |
|
| Improved identification of endogenous peptides from murine nervous tissue by multiplexed peptide extraction methods and multiplexed mass spectrometric analysis. | 2009 Feb |
|
| Studies on the DIDS-binding site of monocarboxylate transporter 1 suggest a homology model of the open conformation and a plausible translocation cycle. | 2009 Jul 24 |
|
| Plasma progranulin levels predict progranulin mutation status in frontotemporal dementia patients and asymptomatic family members. | 2009 Mar |
|
| Oxidative modifications of glyceraldehyde-3-phosphate dehydrogenase play a key role in its multiple cellular functions. | 2009 Sep 25 |
|
| Acute ablation of PERK results in ER dysfunctions followed by reduced insulin secretion and cell proliferation. | 2009 Sep 4 |
|
| Expression and RNA interference of salivary polygalacturonase genes in the tarnished plant bug, Lygus lineolaris. | 2010 |
|
| Oxpholipin 11D: an anti-inflammatory peptide that binds cholesterol and oxidized phospholipids. | 2010 Apr 14 |
|
| Potent homocysteine-induced ERK phosphorylation in cultured neurons depends on self-sensitization via system Xc(-). | 2010 Jan 15 |
|
| Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin. | 2011 |
|
| Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. | 2012 Mar 15 |
Patents
Sample Use Guides
The study was performed with the MG 155 strain of the dermatophyte Microsporum gypseum (ATCC 26 554). For inoculum we used a suspension of spores (100/nL) released from the surface of cultures cultivated for 10 d on Sabouraud's agar (4 % glucose, 1% peptone) at 26C after shaking with glass beads. The medium contained 0.8 % glucose, 0.2 % arginine hydrochloride and 0.04 % potassium dihydrogenphosphate, and was sterilized repeatedly in a stream of steam. As a source of sulphur the basic medium A contained 1 mM sodium sulphate, medium B 3 mM L-cystine and medium C 3 mM DL-cystine. Cystine was added to the sterile medium in the form of a concentrated solution in 1 ~t hydrochloric acid and the medium was immediately neutralized with 1 M potassium hydroxide.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:04:17 UTC 2023
by
admin
on
Sat Dec 16 18:04:17 UTC 2023
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| Record UNII |
06681CV9GH
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| Record Status |
Validated (UNII)
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| Record Version |
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CFR |
21 CFR 862.1240
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06681CV9GH
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m4049
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DTXSID50859005
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923-32-0
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6857538
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203781
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