(2S,3R,4R)-3,4-dihydroxy-2-methoxy-4-methyl-3-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexan-1-one

• ChemBase ID: 3927
• Molecular Formular: C16H26O5
• Molecular Mass: 298.37464
• Monoisotopic Mass: 298.17802393
• SMILES: C1C(=O)[C@H]([C@@]([C@@](C1)(O)C)([C@@]1([C@@H](CC=C(C)C)O1)C)O)OC
• Canonical SMILES: CO[C@@H]1C(=O)CC[C@@]([C@@]1(O)[C@@]1(C)O[C@@H]1CC=C(C)C)(C)O
• InChI: InChI=1S/C16H26O5/c1-10(2)6-7-12-15(4,21-12)16(19)13(20-5)11(17)8-9-14(16,3)18/h6,12-13,18-19H,7-9H2,1-5H3/t12-,13-,14-,15+,16-/m1/s1
• InChIKey: UOXVFQCRPDLSFN-DGXTUMSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R)-3,4-dihydroxy-2-methoxy-4-methyl-3-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexan-1-one
• IUPAC Traditional name: (2S,3R,4R)-3,4-dihydroxy-2-methoxy-4-methyl-3-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexan-1-one
• Synonyms: Ovalicin

Database IDs

• PubChem SID: 160967362; 46507847
• PubChem CID: 5289086

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.587617
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.1463103
• LogD (pH = 7.4): 1.1462826
• Log P: 1.1463107
• Molar Refractivity: 78.6679 cm^3
• Polarizability: 31.233095 Å^3
• Polar Surface Area: 79.29 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.91
• LOG S: -2.12
• Solubility (Water): 2.27e+00 g/l

DETAILS

DrugBank - DB04324

Drug information: experimental