4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-6-hydroxy-2,3,4,5-tetrahydropyridin-2-one

• ChemBase ID: 102108
• Molecular Formular: C15H23NO4
• Molecular Mass: 281.34742
• Monoisotopic Mass: 281.16270822
• SMILES: C[C@H]1C[C@H](C)C(=O)[C@@H](C1)[C@@H](CC1CC(=NC(=O)C1)O)O
• Canonical SMILES: C[C@H]1C[C@H](C)C(=O)[C@@H](C1)[C@@H](CC1CC(=NC(=O)C1)O)O
• InChI: InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1
• InChIKey: YPHMISFOHDHNIV-FSZOTQKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-6-hydroxy-2,3,4,5-tetrahydropyridin-2-one
• IUPAC Traditional name: ActiDione
• Synonyms: Actidone; 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl] glutarimide; Naramycin A; CYCLOHEXIMIDE

Database IDs

• CAS Number: 66-81-9
• EC Number: 200-636-0
• PubChem SID: 162088459
• PubChem CID: 6197

CALCULATED PROPERTIES

• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 7.701156
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2695423
• LogD (pH = 7.4): 1.0962808
• Log P: 1.2722659
• Molar Refractivity: 73.411 cm^3
• Polarizability: 28.880642 Å^3
• Polar Surface Area: 86.96 Å^2

PROPERTIES

Physical Property

• Melting Point: 119.5-121 °C

Safety Information

• Storage Condition: 0°C
• RTECS: MA4375000
• European Hazard Symbols: Nature polluting (N); Highly toxic (T+)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: I
• Australian Hazchem: 2XE
• Risk Statements: R:28-40-51/53-61
• Safety Statements: S:45-53-61
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

DETAILS

MP Biomedicals - 02100183

Crystalline
Inhibits peptide synthesis.

REFERENCES

• Obrig, T.G., et al., J. Biol. Chem., 246: 174 (1971).