(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-methoxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid

• ChemBase ID: 177720
• Molecular Formular: C16H16O10
• Molecular Mass: 368.29224
• Monoisotopic Mass: 368.07434671
• SMILES: O([C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)c1c(cc2c(c1)oc(=O)cc2)OC
• Canonical SMILES: COc1cc2ccc(=O)oc2cc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H16O10/c1-23-8-4-6-2-3-10(17)24-7(6)5-9(8)25-16-13(20)11(18)12(19)14(26-16)15(21)22/h2-5,11-14,16,18-20H,1H3,(H,21,22)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: UTTLUAQBFYOVMO-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-methoxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-methoxy-2-oxochromen-7-yl)oxy]oxane-2-carboxylic acid
• Synonyms: 6-Methoxy-2-oxo-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; Scopoletin β-D-Glucuronide

Database IDs

• CAS Number: 132752-65-9
• PubChem SID: 164233630
• PubChem CID: 25791063

CALCULATED PROPERTIES

• Acid pKa: 2.9067786
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.1724076
• LogD (pH = 7.4): -4.110343
• Log P: -0.62567055
• Molar Refractivity: 82.0045 cm^3
• Polarizability: 32.61719 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S200510

A metabolite of Scopoletin.

REFERENCES

• Ikushiro, S., et al.: Biochemistry, 36, 7154 (1997)
• Ghosh, S.S., et al.: J. Biol. Chem., 276, 42108 (1997)
• Gagne, J.F., et al.: Mol. Pharmacol., 62, 608 (1997)
• Jinno, H., et al.: Drug Metab. Dispos., 31, 108 (1997)