(4R,5S)-3-amino-6-[hydroxy(13C)methyl](2,3,4,5,6-13C5)oxane-2,4,5-triol hydrochloride

• ChemBase ID: 172545
• Molecular Formular: C6H14ClNO5
• Molecular Mass: 221.58798903
• Monoisotopic Mass: 221.07617926
• SMILES: [13C@@H]1([13C@@H]([13CH]([13CH](O[13CH]1[13CH2]O)O)N)O)O.Cl
• Canonical SMILES: O[13CH2][13CH]1O[13CH](O)[13CH]([13C@H]([13C@@H]1O)O)N.Cl
• InChI: InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2?,3?,4-,5-,6?;/m1./s1/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: QKPLRMLTKYXDST-KCUZVKRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-3-amino-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxane-2,4,5-triol hydrochloride
• IUPAC Traditional name: (4R,5S)-3-amino-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxane-2,4,5-triol hydrochloride
• Synonyms: 2-Amino-2-deoxy-D-mannose-13C6 Hydrochloride; D-Mannosamine-13C6 Hydrochloride

Database IDs

• PubChem SID: 164228455
• PubChem CID: 71749903

CALCULATED PROPERTIES

• Acid pKa: 11.726975
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.5965767
• LogD (pH = 7.4): -3.9292529
• Log P: -3.039421
• Molar Refractivity: 37.5809 cm^3
• Polarizability: 15.959335 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M167002

A labelled pharmaceutical compound used in the development of mannosylated liposomes for bioadhesive oral drug delivery via M cells of Peyer's patches.

REFERENCES

• Pukanud, P. et al.: Drug Delivery, 16, 289 (2009)
• Knowles, D.J. et al.: J. Gen. Microbiol., 108, 17 (2009)