(2S,3S,4S,5R,6S)-6-[2-(butoxycarbonyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174706
• Molecular Formular: C18H22O10
• Molecular Mass: 398.36128
• Monoisotopic Mass: 398.1212969
• SMILES: c1ccc(c(c1)C(=O)OCCCC)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCCCOC(=O)c1ccccc1C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H22O10/c1-2-3-8-26-16(24)9-6-4-5-7-10(9)17(25)28-18-13(21)11(19)12(20)14(27-18)15(22)23/h4-7,11-14,18-21H,2-3,8H2,1H3,(H,22,23)/t11-,12-,13+,14-,18-/m0/s1
• InChIKey: SCTNBUBWGRBAFE-PCBYGDGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[2-(butoxycarbonyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[2-(butoxycarbonyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(Butyl 1,2-Benzenedicarboxylate)-β-D-glucopyranuronic Acid; Monobutyl Phthalate Glucuronide; Monobutyl Phthalate Acyl-β-D-glucuronide

Database IDs

• CAS Number: 85209-81-0
• PubChem SID: 164230616
• PubChem CID: 71750780

CALCULATED PROPERTIES

• Acid pKa: 2.7712567
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.4553497
• LogD (pH = 7.4): -2.2858243
• Log P: 1.2104112
• Molar Refractivity: 91.5117 cm^3
• Polarizability: 36.528606 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M525105

Di-n-Butylphthalate (DBP) (M525100) glucuronide metabolite.

REFERENCES

• Shen, O., et al.: Toxicol. Lett., 191, 9 (2009)
• Aylward, L., et al.: Reg. Toxicol. Pharmacol., 55, 259 (2009)
• Beydon, D., et al.: Toxicol. in Vitro, 24, 71 (2009)