(2R)-2-amino-3-{[5-(2H3)acetamido-2-hydroxyphenyl]sulfanyl}propanoic acid; trifluoroacetic acid

• ChemBase ID: 165318
• Molecular Formular: C13H15F3N2O6S
• Molecular Mass: 384.3282096
• Monoisotopic Mass: 384.06029187
• SMILES: c1(ccc(cc1SC[C@H](N)C(=O)O)NC(=O)C)O.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC(=O)Nc1ccc(c(c1)SC[C@@H](C(=O)O)N)O
• InChI: InChI=1S/C11H14N2O4S.C2HF3O2/c1-6(14)13-7-2-3-9(15)10(4-7)18-5-8(12)11(16)17;3-2(4,5)1(6)7/h2-4,8,15H,5,12H2,1H3,(H,13,14)(H,16,17);(H,6,7)/t8-;/m0./s1
• InChIKey: PDZGEXMJHANKLR-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[5-(^2H₃)acetamido-2-hydroxyphenyl]sulfanyl}propanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[5-(^2H₃)acetamido-2-hydroxyphenyl]sulfanyl}propanoic acid; trifluoroacetic acid
• Synonyms: S[5-(Acetylamino)-2-hydroxyphenyl]-L-cysteine-d3 Trifluoroacetic Acid Salt; APAP-CYS-D5 (major), trifluoroacetic acid salt; 3-Cysteinylacetaminophen-D5 (major), Trifluoroacetic Acid Salt

Database IDs

• PubChem SID: 162259451
• PubChem CID: 45038757

CALCULATED PROPERTIES

• Acid pKa: 1.4866731
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.0937717
• LogD (pH = 7.4): -2.1101649
• Log P: -2.0937026
• Molar Refractivity: 69.6437 cm^3
• Polarizability: 26.493248 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Greenish Grey Solid
• Melting Point: 70-75°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C994752

APAP-CYS is a deuterated metabolite of Acetaminophen. Unlabelled APAP-CYS is implicated in nephrotoxicity.Minimum isotopic incorporation d-3, no d-0 present. A representative lot has 64% isotopic incorporation at the 6-position, 89% at the 4-position.