4-hydroxy-3-[(1S)-1-phenylpropyl]-2H,5H,6H,7H,8H,9H-cyclohepta[b]pyran-2-one

• ChemBase ID: 5898
• Molecular Formular: C19H22O3
• Molecular Mass: 298.37618
• Monoisotopic Mass: 298.15689456
• SMILES: c1(c(=O)oc2c(c1O)CCCCC2)[C@H](c1ccccc1)CC
• Canonical SMILES: CC[C@H](c1c(=O)oc2c(c1O)CCCCC2)c1ccccc1
• InChI: InChI=1S/C19H22O3/c1-2-14(13-9-5-3-6-10-13)17-18(20)15-11-7-4-8-12-16(15)22-19(17)21/h3,5-6,9-10,14,20H,2,4,7-8,11-12H2,1H3/t14-/m0/s1
• InChIKey: YKJXQZGJGDTEOC-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[(1S)-1-phenylpropyl]-2H,5H,6H,7H,8H,9H-cyclohepta[b]pyran-2-one
• IUPAC Traditional name: 4-hydroxy-3-[(1S)-1-phenylpropyl]-5H,6H,7H,8H,9H-cyclohepta[b]pyran-2-one
• Synonyms: 6,7,8,9-TETRAHYDRO-4-HYDROXY-3-(1-PHENYLPROPYL)CYCLOHEPTA[B]PYRAN-2-ONE

Database IDs

• PubChem SID: 160969324; 99444745
• PubChem CID: 5289034; 54708746

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.1580606
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.43645
• LogD (pH = 7.4): 4.0074778
• Log P: 4.4458876
• Molar Refractivity: 88.2154 cm^3
• Polarizability: 33.712334 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.38
• LOG S: -4.02
• Solubility (Water): 2.85e-02 g/l

DETAILS

DrugBank - DB08274

Drug information: experimental