(2R)-2-amino-3-{[(2R)-2-amino-2-carboxy(,1,2-13C3)ethyl]disulfanyl}(1,2,3-13C3)propanoic acid

• ChemBase ID: 165324
• Molecular Formular: C6H12N2O4S2
• Molecular Mass: 248.24322682
• Monoisotopic Mass: 248.03804769
• SMILES: S([13CH2][13C@H]([15NH2])[13C](=O)O)S[13CH2][13C@H]([15NH2])[13C](=O)O
• Canonical SMILES: [15NH2][13C@H]([13C](=O)O)[13CH2]SS[13CH2][13C@@H]([13C](=O)O)[15NH2]
• 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/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1
• InChIKey: LEVWYRKDKASIDU-OGYFDXEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(2R)-2-amino-2-carboxy(,1,2-^1^3C₃)ethyl]disulfanyl}(1,2,3-^1^3C₃)propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[(2R)-2-amino-2-carboxy(,1,2-^1^3C₃)ethyl]disulfanyl}(1,2,3-^1^3C₃)propanoic acid
• Synonyms: (-)-Cystine-13C6,15N2; 3,3'-Dithiobis(2-aminopropanoic Acid)-13C6,15N2; Bis(β-amino-β-carboxyethyl)-13C6,15N2 Disulfide; Cystine Αcid-13C6,15N2; Dicysteine-13C6,15N2; 3,3'-Dithiobis-L-alanine-13C6,15N2; L-Cysteine-13C6,15N2 Disulfide; L-Cystin-13C6,15N2; NSC 13203-13C6,15N2; Oxidized-13C6,15N2 L-Cysteine; [R-(R*,R*)]-3,3'-Dithiobis[2-aminopropanoic Acid]-13C6,15N2; l-Cystine-13C6,15N2; β,β'-Diamino-β,β'-dicarboxydiethyl-13C6,15N2 Disulfide; β,β'-Dithiodialanine-13C6,15N2; L-Cystine-13C6,15N2

Database IDs

• PubChem SID: 162259457
• PubChem CID: 71315148

CALCULATED PROPERTIES

• Acid pKa: 1.5564231
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.897319
• LogD (pH = 7.4): -5.9155164
• Log P: -5.897688
• Molar Refractivity: 54.8718 cm^3
• Polarizability: 22.177225 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C997862

Labelled L-Cystine (C997860). L-Cystine is a non-essential amino acid for human development. L-Cystine is formed by the dimerization of two cysteines through the sulfur.

REFERENCES

• Kao, P., et al.: J. Biol.Chem., 261, 8085 ( 1986), Nicke, A., et al.: J. Biol. Chem., 278, 3137 (1977)
• Fahey, R.C., et al.: J. Mol. Evol., 10, 155 (1977)