bis(cyclohexanamine); {[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

• ChemBase ID: 153161
• Molecular Formular: C18H39N2O9P
• Molecular Mass: 458.484021
• Monoisotopic Mass: 458.23931747
• SMILES: C1CCC(CC1)N.C1CCC(CC1)N.C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OP(=O)(O)O)O)O)O)O
• Canonical SMILES: NC1CCCCC1.NC1CCCCC1.OC[C@H]1O[C@@H](OP(=O)(O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/2C6H13N.C6H13O9P/c2*7-6-4-2-1-3-5-6;7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2*6H,1-5,7H2;2-10H,1H2,(H2,11,12,13)/t;;2-,3-,4+,5-,6+/m..1/s1
• InChIKey: YBPDNWXTAIIEAM-LCFXSEKVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(cyclohexanamine); {[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
• IUPAC Traditional name: bis(cyclohexylamine) β-D-glucose 1-phosphate
• Synonyms: β-D-Glucose 1-phosphate bis(cyclohexylammonium) salt

Database IDs

• CAS Number: 14034-70-9
• MDL Number: MFCD00069780
• PubChem SID: 162247301
• PubChem CID: 71311601

CALCULATED PROPERTIES

• Acid pKa: 1.1553719
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -5.503452
• LogD (pH = 7.4): -6.614425
• Log P: -3.0561051
• Molar Refractivity: 46.7963 cm^3
• Polarizability: 19.793747 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Impurities: α-D-Glucose 1-phosphate, essentially free
• Empirical Formula (Hill Notation): C6H13O9P · 2C6H13N

DETAILS

Sigma Aldrich - G7920

Biochem/physiol Actions
β-D-Glucose 1-phosphate is a substrate for β-phosphoglucomutase, which converts it to β-glucose 6-phosphate by forming β-glucose 1,6-diphosphate as an intermediate.1,2 β-Phosphoglucomutase is utilized in both the maltose and trehalose catabolic pathways of lactic acid bacteria, generating β-D-glucose 1-phosphate as a metabolite.3