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

• ChemBase ID: 158351
• Molecular Formular: C6H13ClN2O3S
• Molecular Mass: 228.69702
• Monoisotopic Mass: 228.03354097
• SMILES: CC(=O)NCSC[C@@H](C(=O)O)N.Cl
• Canonical SMILES: CC(=O)NCSC[C@@H](C(=O)O)N.Cl
• InChI: InChI=1S/C6H12N2O3S.ClH/c1-4(9)8-3-12-2-5(7)6(10)11;/h5H,2-3,7H2,1H3,(H,8,9)(H,10,11);1H/t5-;/m0./s1
• InChIKey: SZWPOAKLKGUXDD-JEDNCBNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-[(acetamidomethyl)sulfanyl]propanoic acid hydrochloride
• IUPAC Traditional name: (2R)-2-amino-3-[(acetamidomethyl)sulfanyl]propanoic acid hydrochloride
• Synonyms: H-Cys(Acm).HCl; S-Acetamidomethyl-L-cysteine hydrochloride; S-乙酰氨甲基-L-半胱氨酸 盐酸盐

Database IDs

• CAS Number: 28798-28-9
• EC Number: 249-230-5
• MDL Number: MFCD00077080
• Beilstein Number: 4015821
• PubChem SID: 162252487; 24845008
• PubChem CID: 16211002

CALCULATED PROPERTIES

• Acid pKa: 2.171488
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.73733
• LogD (pH = 7.4): -3.752181
• Log P: -3.7375624
• Molar Refractivity: 45.4121 cm^3
• Polarizability: 18.198801 Å^3
• Polar Surface Area: 92.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~165 °C (dec.)
• Optical Rotation: [α]20/D -28±2°, c = 1% in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (AT)
• Salt Data: HCl
• Empirical Formula (Hill Notation): C6H12N2O3S · HCl
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Sigma Aldrich - 00320

Other Notes
Protected cysteine; cleavage is performed with mercuric acetate or silver nitrate1,2; Oxidative cleavage to disulfides3