[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1Z)-1-(hydroxyimino)-5-(2H3)methanesulfinyl(5,5-2H2)pentyl]sulfanyl}oxan-2-yl]methyl acetate

• ChemBase ID: 166697
• Molecular Formular: C20H31NO11S2
• Molecular Mass: 525.59024
• Monoisotopic Mass: 525.13385282
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)S/C(=N\O)/CCCCS(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: O/N=C(\S[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)/CCCCS(=O)C
• InChI: InChI=1S/C20H31NO11S2/c1-11(22)28-10-15-17(29-12(2)23)18(30-13(3)24)19(31-14(4)25)20(32-15)33-16(21-26)8-6-7-9-34(5)27/h15,17-20,26H,6-10H2,1-5H3/b21-16-/t15-,17-,18+,19-,20+,34?/m1/s1
• InChIKey: RAKGKLGSLMTYBD-GKJUWVKVSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162260830
• PubChem CID: 71315831

CALCULATED PROPERTIES

• Acid pKa: 9.187766
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.93504024
• LogD (pH = 7.4): -0.94193983
• Log P: -0.93494654
• Molar Refractivity: 120.2332 cm^3
• Polarizability: 49.05241 Å^3
• Polar Surface Area: 164.09 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Orange Syrup

DETAILS

Toronto Research Chemicals - D297882

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)