(4S,5S)-6-(aminomethyl)oxane-2,3,4,5-tetrol hydrochloride

• ChemBase ID: 159985
• Molecular Formular: C6H14ClNO5
• Molecular Mass: 215.63206
• Monoisotopic Mass: 215.05605023
• SMILES: [C@@H]1([C@@H](C(C(OC1CN)O)O)O)O.Cl
• Canonical SMILES: NCC1OC(O)C([C@H]([C@@H]1O)O)O.Cl
• InChI: InChI=1S/C6H13NO5.ClH/c7-1-2-3(8)4(9)5(10)6(11)12-2;/h2-6,8-11H,1,7H2;1H/t2?,3-,4+,5?,6?;/m1./s1
• InChIKey: GHQIWWAEPCTDEU-BEPMAALASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-6-(aminomethyl)oxane-2,3,4,5-tetrol hydrochloride
• IUPAC Traditional name: (4S,5S)-6-(aminomethyl)oxane-2,3,4,5-tetrol hydrochloride
• Synonyms: 6-Amino-6-deoxy-D-glucose Hydrochloride

Database IDs

• CAS Number: 55324-97-5
• PubChem SID: 162254120
• PubChem CID: 71313194

CALCULATED PROPERTIES

• Acid pKa: 11.300555
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.7531576
• LogD (pH = 7.4): -4.164267
• 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

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >150°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A603950

An amino sugar used for the synthesis of alkylating nitrogen mustards. These compounds have been studied for potential anti-tumour activity and irreversible enzyme inhibition.

REFERENCES

• Content, S., et al.: Bioorg. Med. Chem. Lett., 13, 321 (2003)