N-cyclohexylcyclohexanaminium (2R)-3-[(2-carbamoyl-2-hydroxyethyl)sulfanyl]-2-(2H3)acetamidopropanoate

• ChemBase ID: 159108
• Molecular Formular: C20H37N3O5S
• Molecular Mass: 431.58988
• Monoisotopic Mass: 431.2453923
• SMILES: [C@@H](CSCC(C(=O)N)O)(NC(=O)C)C(=O)[O-].[NH2+](C1CCCCC1)C1CCCCC1
• Canonical SMILES: C1CCC(CC1)[NH2+]C1CCCCC1.CC(=O)N[C@H](C(=O)[O-])CSCC(C(=O)N)O
• InChI: InChI=1S/C12H23N.C8H14N2O5S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-4(11)10-5(8(14)15)2-16-3-6(12)7(9)13/h11-13H,1-10H2;5-6,12H,2-3H2,1H3,(H2,9,13)(H,10,11)(H,14,15)/t;5-,6?/m.0/s1
• InChIKey: KGIBHDNDPZUJMP-CUUSOBIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-cyclohexylcyclohexanaminium (2R)-3-[(2-carbamoyl-2-hydroxyethyl)sulfanyl]-2-(^2H₃)acetamidopropanoate
• IUPAC Traditional name: dicyclohexylammonium (2R)-3-[(2-carbamoyl-2-hydroxyethyl)sulfanyl]-2-(^2H₃)acetamidopropanoate
• Synonyms: N-Acetyl-S-(3-amino-2-hydroxy-3-oxopropyl)-L-cysteine-d3 Dicyclohexylammonium Salt; N-Acetyl-S-(2-carbamoyl-2-hydroxyethyl)-L-cysteine-d3 Dicyclohexylammonium Salt; GAMA-d3 Dicyclohexylammonium Salt; N-Acetyl-S-(2-hydroxy-3-propionamide)-L-cysteine-d3 Dicyclohexylammonium Salt

Database IDs

• PubChem SID: 162253243
• PubChem CID: 71312804

CALCULATED PROPERTIES

• Acid pKa: 3.6518204
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.23644
• LogD (pH = 7.4): -5.715343
• Log P: -2.391094
• Molar Refractivity: 67.3031 cm^3
• Polarizability: 22.204983 Å^3
• Polar Surface Area: 132.55 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 162-166°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A179132

A labelled metabolite of Acrylamide.

REFERENCES

• Bjellaas, T., et al.: Toxicol. Sci., 100, 374 (2007)
• Doerge, D., et al.: Toxicol. Lett., 169, 34 (2007)
• Hartmann, E., et al.: J. Agric. Food Chem., 56, 6061 (2007)