(2S)-2-amino-3-{[carboxy(13C2)methyl]sulfanyl}(1-13C)propanoic acid

• ChemBase ID: 163775
• Molecular Formular: C5H9NO4S
• Molecular Mass: 182.17222451
• Monoisotopic Mass: 182.03529329
• SMILES: [13C](=O)([13CH2]SC[C@@H]([13C](=O)O)N)O
• Canonical SMILES: O[13C](=O)[13CH2]SC[C@@H]([13C](=O)O)N
• InChI: InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1/i2+1,4+1,5+1
• InChIKey: GBFLZEXEOZUWRN-WCENHBHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{[carboxy(^1^3C₂)methyl]sulfanyl}(1-^1^3C)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{[carboxy(^1^3C₂)methyl]sulfanyl}(1-^1^3C)propanoic acid
• Synonyms: S-Carboxymethyl-L-cysteine-13C3; (2R)-2-Amino-3-[(carboxymethyl)thio]propionic Acid-13C3; (R)-S-(Carboxymethyl)cysteine-13C3; (L)-2-Amino-3-(carboxymethylthio)propionic Acid-13C3; 3-[(Carboxymethyl)thio]-L-alanine-13C3; AHR 3053-13C3; Bronchokod-13C3; Carbocisteine-13C3; Carbocit-13C3; Carbocysteine-13C3; Chilvax-13C3; DF 1794Y-13C3; L-(Carboxymethyl)cysteine-13C3; LJ 206-13C3; Lisil-13C3; Lisomucil-13C3; Loviscol-13C3; Muciclar-13C3; Mucocis-13C3; Mucodyne-13C3; Mucofan-13C3; Mucolase-13C3; Mucolex-13C3; Mucopront-13C3; Mucosol-13C3; Mucotab-13C3; Mukinyl; -13C3 NSC 14156-13C3; PectDrill-13C3; Pectox-13C3; Pulmoclase-13C3; Reomucil-13C3; Rhinathiol-13C3; Rhinatiol-13C3; Rinatiol-13C3; S-(Carboxymethyl)-(R)-cysteine-13C3; S-Carboxylmethyl-L-cysteine-13C3; Siroxyl-13C3; Thiodril-13C3; Transbronchin-13C3; Carbocisteine-13C3

Database IDs

• PubChem SID: 162257910
• PubChem CID: 71314549

CALCULATED PROPERTIES

• Acid pKa: 1.8428031
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.6978083
• LogD (pH = 7.4): -6.374103
• Log P: -3.297409
• Molar Refractivity: 39.1068 cm^3
• Polarizability: 15.744593 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C178762

Labelled Carbocisteine (C178760). Carbocisteine is a mucolytic agent used in the treatment of respiratory disorders ranging from the influenza virus infection to chronic obstructive pulmonary disease (COPD).

REFERENCES

• Stevenson, G.B. et al.: Eur. Resp. J., 27, 865 (2006)
• Suer, E. et al.: J. Infect. Chemother., 14, 333 (2006)
• Yamaya, M. et al.: Am. J. Physiol., 299, L160 (2006)