{[(2R,3S,4R,5R)-5-amino-3,4,6-trihydroxy(2,3,4,5,6-13C5)oxan-2-yl](13C)methoxy}phosphonic acid hydrate

• ChemBase ID: 169665
• Molecular Formular: C6H16NO9P
• Molecular Mass: 283.12223003
• Monoisotopic Mass: 283.07639676
• SMILES: [13C@@H]1([13C@@H]([13C@@H]([13CH](O[13C@H]1[13CH2]OP(=O)(O)O)O)N)O)O.O
• Canonical SMILES: O[13CH]1O[13C@@H]([13CH2]OP(=O)(O)O)[13C@H]([13C@@H]([13C@@H]1N)O)O.O
• InChI: InChI=1S/C6H14NO8P.H2O/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13;/h2-6,8-10H,1,7H2,(H2,11,12,13);1H2/t2-,3-,4-,5-,6?;/m1./s1/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: WFVOZJAYZYVDTL-CBIGNMKJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-amino-3,4,6-trihydroxy(2,3,4,5,6-^1^3C₅)oxan-2-yl](^1^3C)methoxy}phosphonic acid hydrate
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-amino-3,4,6-trihydroxy(2,3,4,5,6-^1^3C₅)oxan-2-yl](^1^3C)methoxyphosphonic acid hydrate
• Synonyms: 2-Amino-2-deoxy-D-glucose-13C6 6-(Dihydrogen Phosphate) Hydrate; Glucosamine-13C6 6-Phosphate Hydrate; 2-Amino-2-deoxy-D-glucose-13C6 6-Phosphate Hydrate; 2-Amino-2-deoxyglucose-13C6 6-Phosphate Hydrate; 2-Amino-D-glucose-6-phosphate-13C6 Hydrate; D-Glucosamine-13C6 6-Phosphate Hydrate; D-Glucosamine-13C6 6-Phosphate Hydrate

Database IDs

• PubChem SID: 162263797
• PubChem CID: 71317090

CALCULATED PROPERTIES

• Acid pKa: 1.22317
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -4.2442045
• LogD (pH = 7.4): -5.385255
• Log P: -4.1756725
• Molar Refractivity: 48.4538 cm^3
• Polarizability: 20.562544 Å^3
• Polar Surface Area: 162.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G515052

Labelled Galactosamine-6-phosphate. It was identified as a component of the coat of the Bacillus megaterium QM B1551 spore. It was one of the main constituents of the outermost layer of the spore coat, but it was absent from the other integuments includi

REFERENCES

• Dabich, D., et al.: J. Biol. Chem., 241, 415 (1966)
• Nasu M., et al.: Microb. Immunol., 28, 181 (1966)