(2R)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid

• ChemBase ID: 2211
• Molecular Formular: C5H9NO4S
• Molecular Mass: 179.19426
• Monoisotopic Mass: 179.02522877
• SMILES: N[C@@H](CSCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CSC[C@@H](C(=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
• InChIKey: GBFLZEXEOZUWRN-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid
• IUPAC Traditional name: carboxymethylated cysteine; carboxymethylenecysteine; carbocisteine
• Synonyms: Carbocysteine; 1-Carboxymethylcysteine; 3-(Carboxymethylthio)alanine; S-CARBOXYMETHYL-L-CYSTEINE; 3-carboxymethylthio-L-alanine; S-Carboxymethyl-L-cysteine; (2R)-2-Amino-3-[(carboxymethyl)thio]propionic Acid; (R)-S-(Carboxymethyl)cysteine; (L)-2-Amino-3-(carboxymethylthio)propionic Acid; 3-[(Carboxymethyl)thio]-L-alanine; AHR 3053; Bronchokod; Carbocisteine; Carbocit; Chilvax; DF 1794Y; L-(Carboxymethyl)cysteine; LJ 206; Lisil; Lisomucil; Loviscol; Muciclar; Mucocis; Mucodyne; Mucofan; Mucolase; Mucolex; Mucopront; Mucosol; Mucotab; Mukinyl; NSC 14156; PectDrill; Pectox; Pulmoclase; Reomucil; Rhinathiol; Rhinatiol; Rinatiol; S-(Carboxymethyl)-(R)-cysteine; S-Carboxylmethyl-L-cysteine; Siroxyl; Thiodril; Transbronchin; Carbocisteine; Carboxymethylated Cysteine; Carboxymethylenecysteine; S-Carboxymethyl-L-cysteine; S-(Carboxymethyl)-L-Cysteine; 3-羧甲基硫代-L-丙氨酸; S-羧甲基-L-半胱氨酸; S-羟甲基-L-半胱氨酸

Database IDs

• CAS Number: 638-23-3
• EC Number: 211-327-5
• MDL Number: MFCD00002614
• Beilstein Number: 1725012
• Merck Index: 141802
• PubChem SID: 46507988; 24892985; 160965664
• PubChem CID: 193653

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -3.2
• LOG S: -0.92
• Solubility (Water): 2.16e+01 g/l

PROPERTIES

Physical Property

• Melting Point: 200°C; ca 200°C dec.
• Optical Rotation: -29 (c=10 in 10% NaHCO)

Safety Information

• Storage Condition: 2-8°C
• RTECS: AY4342000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: R:22
• Safety Statements: S:36/37/39
• TSCA Listed: 是
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C5H9NO4S

DETAILS

MP Biomedicals - 02101276

Crystalline

DrugBank - DB04339

Drug information: experimental

DrugBank - DB02476

Drug information: experimental

Toronto Research Chemicals - 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)