cyclohexanaminium [(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(2-nitrophenoxy)oxan-2-yl]methyl hydrogen phosphate

• ChemBase ID: 175343
• Molecular Formular: C18H29N2O11P
• Molecular Mass: 480.403421
• Monoisotopic Mass: 480.15089639
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COP(=O)([O-])O)Oc1ccccc1[N+](=O)[O-])O)O)O.C1(CCCCC1)[NH3+]
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@@H]1O)COP(=O)(O)[O-])Oc1ccccc1[N+](=O)[O-].[NH3+]C1CCCCC1
• InChI: InChI=1S/C12H16NO11P.C6H13N/c14-9-8(5-22-25(19,20)21)24-12(11(16)10(9)15)23-7-4-2-1-3-6(7)13(17)18;7-6-4-2-1-3-5-6/h1-4,8-12,14-16H,5H2,(H2,19,20,21);6H,1-5,7H2/t8-,9+,10+,11-,12-;/m1./s1
• InChIKey: GYBRWPWCTCQBFW-YOGPMPDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohexanaminium [(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(2-nitrophenoxy)oxan-2-yl]methyl hydrogen phosphate
• IUPAC Traditional name: cyclohexylammonium ion [(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(2-nitrophenoxy)oxan-2-yl]methyl hydrogen phosphate
• Synonyms: o-Nitrophenyl β-D-Galactopyranoside-6-phosphate, Cyclohexylammonium Salt,

Database IDs

• CAS Number: 25405-62-3
• PubChem SID: 164231253
• PubChem CID: 71751094

CALCULATED PROPERTIES

• Acid pKa: 1.2228793
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -3.2239206
• LogD (pH = 7.4): -4.314109
• Log P: -0.7819694
• Molar Refractivity: 77.2592 cm^3
• Polarizability: 31.111248 Å^3
• Polar Surface Area: 194.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 160-163°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N503625

A substrate for staphylococcal β-galactosidase, an enzyme that cleaves the glycosidic bond in phosphorylated β-galactosides.

REFERENCES

• Hengstenberg, W., et al.: Proc. Natl. Acad. Sci. USA, 58, 274 (1967)
• Kennedy, E.P. and Scarborough, G.A.: Proc. Natl. Acad. Sci. USA, 58, 225 (1967)