(2R)-2-amino-3-{[2-hydroxy(2H4)ethyl]sulfanyl}propanoic acid

• ChemBase ID: 170538
• Molecular Formular: C5H11NO3S
• Molecular Mass: 165.21074
• Monoisotopic Mass: 165.04596422
• SMILES: C(SC[C@H](N)C(=O)O)CO
• Canonical SMILES: OCCSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H11NO3S/c6-4(5(8)9)3-10-2-1-7/h4,7H,1-3,6H2,(H,8,9)/t4-/m0/s1
• InChIKey: MWFRVMDVLYIXJF-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[2-hydroxy(^2H₄)ethyl]sulfanyl}propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[2-hydroxy(^2H₄)ethyl]sulfanyl}propanoic acid
• Synonyms: 3-(2-Hydroxyethylthio-d4)alanine; (2R)-2-Amino-3-[(2-hydroxyethyl-d4)sulfanyl]propionic Acid; (S)-2-Hydroxyethyl-d4-L-cysteine; 3-(β-Hydroxyethyl-d4-thio)alanine; 3-[(2-Hydroxyethyl-d4)thio]-L-alanine; S-(2-Hydroxyethyl-d4)-L-cysteine

Database IDs

• PubChem SID: 164226448
• PubChem CID: 71749020

CALCULATED PROPERTIES

• Acid pKa: 2.2558057
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.3549123
• LogD (pH = 7.4): -3.3620284
• Log P: -3.3549755
• Molar Refractivity: 39.3701 cm^3
• Polarizability: 15.741252 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941982

A labelled metabolite of ethylene oxide.

REFERENCES

• Guengerich, F., et al.: Chem. Res. Toxicol., 4, 168 (1991)
• Giri, A., et al.: Mutation Res., 339, 1 (1991)
• Cullinan, D., et al.: J. Mol. Biol., 296, 851(1991)