(2R)-3-[(1-cyano-2-hydroxyethyl)sulfanyl]-2-acetamidopropanoic acid; N-cyclohexylcyclohexanamine

• ChemBase ID: 159210
• Molecular Formular: C20H35N3O4S
• Molecular Mass: 413.5746
• Monoisotopic Mass: 413.23482762
• SMILES: OCC(SC[C@H](NC(=O)C)C(=O)O)C#N.C1(NC2CCCCC2)CCCCC1
• Canonical SMILES: C1CCC(CC1)NC1CCCCC1.OCC(C#N)SC[C@@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C12H23N.C8H12N2O4S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-5(12)10-7(8(13)14)4-15-6(2-9)3-11/h11-13H,1-10H2;6-7,11H,3-4H2,1H3,(H,10,12)(H,13,14)/t;6?,7-/m.0/s1
• InChIKey: AEWZVNHASHNRAX-IOKFPZHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-[(1-cyano-2-hydroxyethyl)sulfanyl]-2-acetamidopropanoic acid; N-cyclohexylcyclohexanamine
• IUPAC Traditional name: (2R)-3-[(1-cyano-2-hydroxyethyl)sulfanyl]-2-acetamidopropanoic acid; dicha
• Synonyms: N-Acetyl-S-(1-cyano-2-hydroxyethyl)cysteine Dicyclohexylamine Salt; N-Acetyl-S-(1-cyano-2-hydroxyethyl)-L-cysteine Dicyclohexylamine Salt(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162253345
• PubChem CID: 57347626

CALCULATED PROPERTIES

• Acid pKa: 2.1129708
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.729509
• LogD (pH = 7.4): -5.099801
• Log P: -1.5778509
• Molar Refractivity: 53.5675 cm^3
• Polarizability: 20.913927 Å^3
• Polar Surface Area: 110.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: >170°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A172080

A metabolite of Acrylonitrile (ACN).

REFERENCES

• Guengerich, F., et al.: Cancer Res., 41, 4925 (1981)
• Leonard, A., et al.: Mutation Res., 436, 263 (1981)
• Stadler, R., et al.: J. Agric. Food Chem., 52, 5550 (1981)
• Dybing, E., et al.: Food Chem. Toxicol., 43, 365 (1981)
• Rice, J., et al.: Mutation Res.