prop-2-en-1-yl (3S,5S,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylate

• ChemBase ID: 178708
• Molecular Formular: C24H27NO9
• Molecular Mass: 473.47248
• Monoisotopic Mass: 473.16858145
• SMILES: c1cc(n(c1C(=O)c1ccc(cc1)C)C)CC(=O)O[C@@H]1OC([C@H](C([C@H]1O)O)O)C(=O)OCC=C
• Canonical SMILES: C=CCOC(=O)C1O[C@@H](OC(=O)Cc2ccc(n2C)C(=O)c2ccc(cc2)C)[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C24H27NO9/c1-4-11-32-23(31)22-20(29)19(28)21(30)24(34-22)33-17(26)12-15-9-10-16(25(15)3)18(27)14-7-5-13(2)6-8-14/h4-10,19-22,24,28-30H,1,11-12H2,2-3H3/t19?,20-,21-,22?,24+/m0/s1
• InChIKey: AKAOKCUSPLBNCM-LBWLBHBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (3S,5S,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylate
• IUPAC Traditional name: prop-2-en-1-yl (3S,5S,6S)-3,4,5-trihydroxy-6-({2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl}oxy)oxane-2-carboxylate
• Synonyms: 1-[1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate]β-D-Glucopyranuronic Acid Allyl Ester; Tolmetin Glucuronide Allyl Ester; Tolmetin β-D-Glucuronide Allyl Ester

Database IDs

• PubChem SID: 164234618
• PubChem CID: 71752609

CALCULATED PROPERTIES

• Acid pKa: 12.161992
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.6566812
• LogD (pH = 7.4): 1.6566738
• Log P: 1.6566813
• Molar Refractivity: 118.6232 cm^3
• Polarizability: 46.703144 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Green-Yellow Solid

DETAILS

Toronto Research Chemicals - T535370

Protected Tolmetin metabolite.