cyclohexanamine; {[(2R,3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy}phosphonic acid

• ChemBase ID: 169729
• Molecular Formular: C13H28NO10P
• Molecular Mass: 389.335881
• Monoisotopic Mass: 389.14508273
• SMILES: C1(CCCCC1)N.[C@@H]1([C@H]([C@@H]([C@H](O[C@H]1OP(=O)(O)O)[C@@H](CO)O)O)O)O
• Canonical SMILES: NC1CCCCC1.OC[C@H]([C@H]1O[C@@H](OP(=O)(O)O)[C@H]([C@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C7H15O10P.C6H13N/c8-1-2(9)6-4(11)3(10)5(12)7(16-6)17-18(13,14)15;7-6-4-2-1-3-5-6/h2-12H,1H2,(H2,13,14,15);6H,1-5,7H2/t2-,3+,4+,5+,6-,7-;/m1./s1
• InChIKey: VPZKBMXIQJKYSY-CGXRMXJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohexanamine; {[(2R,3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphosphonic acid; cyclohexylamine
• Synonyms: (D-Glycero-α-D-manno-heptopyranosyl)-dihydogenphosphate, Cyclohexylammonium Salt

Database IDs

• CAS Number: 359435-45-3
• PubChem SID: 162263861
• PubChem CID: 71317127

CALCULATED PROPERTIES

• Acid pKa: 1.1553241
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -6.133795
• LogD (pH = 7.4): -7.2448025
• Log P: -3.6864402
• Molar Refractivity: 52.7588 cm^3
• Polarizability: 22.305922 Å^3
• Polar Surface Area: 177.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Powder
• Melting Point: 139-142°C

DETAILS

Toronto Research Chemicals - G598580

Key intermediate in the metabolism of sugars and their transformation to nucleotides. Also a potential inhibitor for the heptose synthetase, an enzyme of the biosynthesis of the inner core region of lipopolysaccharides.Contains 1-2 equivalents of cyclohe

REFERENCES

• Paulsen, H., et al.: Liebigs Ann. Chem., 389 (1994)