2,3-dimethyl (1S,4R)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

• ChemBase ID: 5562
• Molecular Formular: C22H18O7
• Molecular Mass: 394.37412
• Monoisotopic Mass: 394.10525292
• SMILES: c1cc(O)ccc1C1=C([C@@H]2O[C@H]1C(=C2C(=O)OC)C(=O)OC)c1ccc(O)cc1
• Canonical SMILES: COC(=O)C1=C(C(=O)OC)[C@H]2O[C@@H]1C(=C2c1ccc(cc1)O)c1ccc(cc1)O
• InChI: InChI=1S/C22H18O7/c1-27-21(25)17-18(22(26)28-2)20-16(12-5-9-14(24)10-6-12)15(19(17)29-20)11-3-7-13(23)8-4-11/h3-10,19-20,23-24H,1-2H3/t19-,20+
• InChIKey: CRLQCBACIMUGDZ-BGYRXZFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dimethyl (1S,4R)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
• IUPAC Traditional name: 2,3-dimethyl (1S,4R)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
• Synonyms: dimethyl (1R,4S)-5,6-bis(4-hydroxyphenyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Database IDs

• PubChem SID: 99444403; 160968990
• PubChem CID: 11531308

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.9054785
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.0085242
• LogD (pH = 7.4): 2.995289
• Log P: 3.0086942
• Molar Refractivity: 103.3045 cm^3
• Polarizability: 40.004105 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.64
• LOG S: -4.62
• Solubility (Water): 9.42e-03 g/l

DETAILS

DrugBank - DB07932

Drug information: experimental