(2R,3R,4R,5S,6S)-6-[2,2-bis(bromomethyl)-3-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176300
• Molecular Formular: C11H18Br2O8
• Molecular Mass: 438.06382
• Monoisotopic Mass: 435.93684154
• SMILES: C(CO[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)(CBr)(CO)CBr
• Canonical SMILES: OCC(CO[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)(CBr)CBr
• InChI: InChI=1S/C11H18Br2O8/c12-1-11(2-13,3-14)4-20-10-7(17)5(15)6(16)8(21-10)9(18)19/h5-8,10,14-17H,1-4H2,(H,18,19)/t5-,6-,7+,8-,10+/m1/s1
• InChIKey: JQFPAHSMEUXVKF-GBMPTNJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-6-[2,2-bis(bromomethyl)-3-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-6-[2,2-bis(bromomethyl)-3-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2,2-Bis(bromomethyl)-1,3-propanediol β-D-Glucopyranosiduronic Acid; Pentaerythritol Dibromide β-D-Glucuronide

Database IDs

• CAS Number: 1138247-37-6
• PubChem SID: 164232210
• PubChem CID: 71751501

CALCULATED PROPERTIES

• Acid pKa: 2.7689364
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -3.7767324
• LogD (pH = 7.4): -4.605379
• Log P: -1.1089734
• Molar Refractivity: 76.0774 cm^3
• Polarizability: 31.028656 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P269975

A metabolite of Pentaerythritol dibromide.

REFERENCES

• Birnbaum, L., et al.: Toxicol. Appl. Pharmacol., 55, 342 (1980)
• Court, M., et al.: J. Pharmacol. Exp. Ther., 299, 998 (1980)
• Diehl, K., et al.: J. Appl. Toxicol., 21, 15 (1980)
• Knudsen, G., et al.: Toxicology, 237, 158 (1980)
• Sakamoto, S., et al.: Dru