Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB120299 |
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Identification |
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Name: |
L-cystine |
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Description: | 20 November 2014 |
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Structure |
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Synonyms: | - (2R,2'R)-3,3'-dithiobis(2-ammoniopropanoate)
- L-cystine
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Chemical Formula: |
C6H12N2O4S2 |
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Average Molecular Weight: |
240.292 |
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Monoisotopic Molecular
Weight: |
242.0395 |
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InChI Key: |
LEVWYRKDKASIDU-IMJSIDKUSA-N |
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InChI: | 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-/m0/s1 |
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CAS
number: |
56-89-3 |
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IUPAC Name: | (2R,2'R)-3,3'-disulfanediylbis(2-ammoniopropanoate) |
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Traditional IUPAC Name: |
L-cystine |
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SMILES: | C(C(C(=O)[O-])[N+])SSCC(C([O-])=O)[N+] |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated. |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organic acids and derivatives |
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Sub Class | Carboxylic acids and derivatives |
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Direct Parent |
L-cysteine-S-conjugates |
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Alternative Parents |
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Substituents |
- L-cysteine-s-conjugate
- Alpha-amino acid
- L-alpha-amino acid
- Dicarboxylic acid or derivatives
- Organic disulfide
- Dialkyldisulfide
- Amino acid
- Sulfenyl compound
- Carboxylic acid
- Organopnictogen compound
- Organic nitrogen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework |
Aliphatic acyclic compounds |
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External Descriptors |
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Physical Properties |
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State: |
Solid |
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Charge: | 0 |
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Melting point: |
260.5 °C |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | 260.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.19 mg/mL | Not Available | LogP | -5.08 | CHMELIK,J ET AL. (1991) |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-00kb-0950000000-a803bc05843192dd737d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | splash10-00kb-0940000000-f82b905ef9e7c9e47552 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-00di-9850000000-49b9a52a8387d6d6f272 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-014j-1970000000-9576699202733d4fd7ed | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-0890000000-51a32ee40240e45646bc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9700000000-4054924ddfb90f120e67 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9100000000-085d45702e61de0f8e4d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available |
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MS | Mass Spectrum (Electron Ionization) | splash10-000x-9000000000-ae0f516d71e6a49fe52f | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 13C NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 13C NMR Spectrum | Not Available |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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References |
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References: |
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [2026685 ]
- Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [12834252 ]
- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [14992292 ]
- Rumpold H, Mascher K, Untergasser G, Plas E, Hermann M, Berger P: Trans-differentiation of prostatic stromal cells leads to decreased glycoprotein hormone alpha production. J Clin Endocrinol Metab. 2002 Nov;87(11):5297-303. [12414905 ]
- Alexander S, Ison C: Evaluation of commercial kits for the identification of Neisseria gonorrhoeae. J Med Microbiol. 2005 Sep;54(Pt 9):827-31. [16091433 ]
- Terada T, Maeda H, Okamoto K, Nishinaka T, Mizoguchi T, Nishihara T: Modulation of glutathione S-transferase activity by a thiol/disulfide exchange reaction and involvement of thioltransferase. Arch Biochem Biophys. 1993 Jan;300(1):495-500. [8424686 ]
- Sonies BC, Almajid P, Kleta R, Bernardini I, Gahl WA: Swallowing dysfunction in 101 patients with nephropathic cystinosis: benefit of long-term cysteamine therapy. Medicine (Baltimore). 2005 May;84(3):137-46. [15879904 ]
- Mogil'naia GM, Shubich MG: [Comparison of the histochemical bases of epidermis differentiation in vertebrates] Arkh Anat Gistol Embriol. 1976 Mar;70(3):46-52. [1275714 ]
- Peters T, Thaete C, Wolf S, Popp A, Sedlmeier R, Grosse J, Nehls MC, Russ A, Schlueter V: A mouse model for cystinuria type I. Hum Mol Genet. 2003 Sep 1;12(17):2109-20. [12923163 ]
- Park M, Helip-Wooley A, Thoene J: Lysosomal cystine storage augments apoptosis in cultured human fibroblasts and renal tubular epithelial cells. J Am Soc Nephrol. 2002 Dec;13(12):2878-87. [12444206 ]
- Rossi S, Herrine SK, Navarro VJ: Cystinosis as a cause of noncirrhotic portal hypertension. Dig Dis Sci. 2005 Jul;50(7):1372-5. [16047489 ]
- Sakhaee K: Pathogenesis and medical management of cystinuria. Semin Nephrol. 1996 Sep;16(5):435-47. [8890399 ]
- Orakzai N, Hanbury DC, Farrington K: Screening for biochemical abnormalities in urolithiasis patients. J Ayub Med Coll Abbottabad. 2004 Apr-Jun;16(2):60-3. [15455621 ]
- Mitchell BF, Chibbar R: Synthesis and metabolism of oxytocin in late gestation in human decidua. Adv Exp Med Biol. 1995;395:365-80. [8713992 ]
- Behr T, Becker W, Hannappel E, Goldenberg DM, Wolf F: 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. Cancer Res. 1995 Dec 1;55(23 Suppl):5777s-5785s. [7493346 ]
- Coe FL, Evan A, Worcester E: Kidney stone disease. J Clin Invest. 2005 Oct;115(10):2598-608. [16200192 ]
- Kubilus J, MacDonald MJ, Baden HP: Epidermal proteins of cultured human and bovine keratinocytes. Biochim Biophys Acta. 1979 Jun 19;578(2):484-92. [486533 ]
- Tezuka T, Takahashi M: The cystine-rich envelope protein from human epidermal stratum corneum cells. J Invest Dermatol. 1987 Jan;88(1):47-51. [3794387 ]
- Worcester EM, Coe FL, Evan AP, Parks JH: Reduced renal function and benefits of treatment in cystinuria vs other forms of nephrolithiasis. BJU Int. 2006 Jun;97(6):1285-90. [16686727 ]
- Allen JW, Shanker G, Tan KH, Aschner M: The consequences of methylmercury exposure on interactive functions between astrocytes and neurons. Neurotoxicology. 2002 Dec;23(6):755-9. [12520765 ]
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Synthesis Reference: |
Grossi, Loris; Montevecchi, Pier Carlo. S-Nitrosocysteine and Cystine from Reaction of Cysteine with Nitrous Acid. A Kinetic Investigation. Journal of Organic Chemistry (2002), 67(24), 8625-8630. |
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Material Safety Data Sheet (MSDS) |
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Links |
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External Links: |
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