(2S,3R,4S,5S,6R)-2-{[(1Z)-1-(hydroxyimino)-5-(2H3)methanesulfinyl(5,5-2H2)pentyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 166701
• Molecular Formular: C12H23NO7S2
• Molecular Mass: 357.44352
• Monoisotopic Mass: 357.09159408
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)S/C(=N\O)/CCCCS(=O)C)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](S/C(=N\O)/CCCCS(=O)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H23NO7S2/c1-22(19)5-3-2-4-8(13-18)21-12-11(17)10(16)9(15)7(6-14)20-12/h7,9-12,14-18H,2-6H2,1H3/b13-8-/t7-,9-,10+,11-,12+,22?/m1/s1
• InChIKey: UYHMVWFYYZIVOP-OGNZPLCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(1Z)-1-(hydroxyimino)-5-(^2H₃)methanesulfinyl(5,5-^2H₂)pentyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-2-{[(1Z)-1-(hydroxyimino)-5-(^2H₃)methanesulfinyl(5,5-^2H₂)pentyl]sulfanyl}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 1-Thio-1-[N-hydroxy-5-(methylsulfinyl)pentanimidate]-d5 β-D-Glucopyranose; 4-Methylsulfinylbutyldesulfoglucosinolate-d5; Desulfo Glucoraphanin-d5

Database IDs

• PubChem SID: 162260834
• PubChem CID: 71315836

CALCULATED PROPERTIES

• Acid pKa: 9.395626
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.6995087
• LogD (pH = 7.4): -2.703795
• Log P: -2.699448
• Molar Refractivity: 83.6272 cm^3
• Polarizability: 33.623367 Å^3
• Polar Surface Area: 139.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D297912

Labelled glucosinolate analog of Glucoraphanin found in cruciferous vegetables such as broccoli and cauliflower.

REFERENCES

• Lee, J.G. et al.: Horticult. Env. Biotech., 50, 509 (2009)
• KIm, J.K. et al.: Food Chem., 119, 423 (2009)