(2R,4R,5R)-5-[(1S)-1-acetamido-3-methylbutyl]-4-(methoxycarbonyl)oxolane-2-carboxylic acid

• ChemBase ID: 2954
• Molecular Formular: C14H23NO6
• Molecular Mass: 301.33552
• Monoisotopic Mass: 301.15253746
• SMILES: [C@@H]1([C@@H](O[C@H](C1)C(=O)O)[C@@H](NC(=O)C)CC(C)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1C[C@@H](O[C@H]1[C@@H](NC(=O)C)CC(C)C)C(=O)O
• InChI: InChI=1S/C14H23NO6/c1-7(2)5-10(15-8(3)16)12-9(14(19)20-4)6-11(21-12)13(17)18/h7,9-12H,5-6H2,1-4H3,(H,15,16)(H,17,18)/t9-,10+,11-,12-/m1/s1
• InChIKey: MUJPWSPVNZGJOW-WRWGMCAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-5-[(1S)-1-acetamido-3-methylbutyl]-4-(methoxycarbonyl)oxolane-2-carboxylic acid
• IUPAC Traditional name: (2R,4R,5R)-5-[(1S)-1-acetamido-3-methylbutyl]-4-(methoxycarbonyl)oxolane-2-carboxylic acid
• Synonyms: 5-[1-(Acetylamino)-3-Methylbutyl]-2,5-Anhydro-3,4-Dideoxy-4-(Methoxycarbonyl)Pentonic Acid

Database IDs

• PubChem SID: 46506456; 160966401
• PubChem CID: 449201

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8859835
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.1220859
• LogD (pH = 7.4): -2.7236419
• Log P: 0.49714756
• Molar Refractivity: 72.3946 cm^3
• Polarizability: 29.113537 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.82
• LOG S: -1.51
• Solubility (Water): 9.29e+00 g/l

DETAILS

DrugBank - DB03257

Drug information: experimental