(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2H9)pyren-1-yloxy]oxane-2-carboxylic acid

• ChemBase ID: 171239
• Molecular Formular: C22H18O7
• Molecular Mass: 394.37412
• Monoisotopic Mass: 394.10525292
• SMILES: c12cccc3c1c1c(cc3)ccc(c1cc2)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)O)Oc1ccc2c3c1ccc1c3c(cc2)ccc1
• InChI: InChI=1S/C22H18O7/c23-17-18(24)20(21(26)27)29-22(19(17)25)28-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9,17-20,22-25H,(H,26,27)/t17-,18-,19+,20-,22+/m0/s1
• InChIKey: BUCREAQPYGLZLI-SXFAUFNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(^2H₉)pyren-1-yloxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(^2H₉)pyren-1-yloxy]oxane-2-carboxylic acid
• Synonyms: 1-Pyrenyl-d9 β-D-Glucopyranosiduronic Acid; 1-Hydroxypyrene-d9 Glucuronide; 1-Hydroxypyrene-d9 β-D-Glucuronide

Database IDs

• PubChem SID: 164227149
• PubChem CID: 71749318

CALCULATED PROPERTIES

• Acid pKa: 3.7831345
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.31408197
• LogD (pH = 7.4): -1.2374847
• Log P: 2.0325687
• Molar Refractivity: 100.7153 cm^3
• Polarizability: 43.49289 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Tan Solid
• Melting Point: >175°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H952752

A labelled metabolite of 1-Hydroxypyrene, which is found in human urine after exposure to coal tar and a coal derived product.

REFERENCES

• Jongeneelen, F.J., et al.: Int. Arch. Occup. Environ. Health, 57, 47 (1985)