(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

• ChemBase ID: 312968
• Molecular Formular: C15H20ClNO4
• Molecular Mass: 313.7766
• Monoisotopic Mass: 313.10808581
• SMILES: C1(=O)O[C@@]2([C@]1(NC(=O)[C@@H]2CCCl)[C@H]([C@@H]1C=CCCC1)O)C
• Canonical SMILES: ClCC[C@H]1C(=O)N[C@@]2([C@@]1(C)OC2=O)[C@H]([C@H]1CCCC=C1)O
• InChI: InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1
• InChIKey: NGWSFRIPKNWYAO-SHTIJGAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• IUPAC Traditional name: salinosporamide A
• Synonyms: ML858; Salinosporamide A (NPI-0052, Marizomib)

Database IDs

• CAS Number: 437742-34-2

CALCULATED PROPERTIES

• Acid pKa: 9.567817
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2398018
• LogD (pH = 7.4): 1.2372301
• Log P: 1.2398348
• Molar Refractivity: 77.3853 cm^3
• Polarizability: 30.450653 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Target: Proteasome

Product Information

• Salt Data: Free Base