[2,3-dihydroxy(1,2,3-13C3)propoxy]phosphonic acid; cyclohexanamine

• ChemBase ID: 169731
• Molecular Formular: C9H22NO6P
• Molecular Mass: 274.22580551
• Monoisotopic Mass: 274.12853857
• SMILES: O[13CH2][13CH]([13CH2]OP(=O)(O)O)O.C1CCCC(C1)N
• Canonical SMILES: NC1CCCCC1.O[13CH2][13CH]([13CH2]OP(=O)(O)O)O
• InChI: InChI=1S/C6H13N.C3H9O6P/c7-6-4-2-1-3-5-6;4-1-3(5)2-9-10(6,7)8/h6H,1-5,7H2;3-5H,1-2H2,(H2,6,7,8)/i;1+1,2+1,3+1
• InChIKey: KRPIJKAIDSXSIO-BURVIEGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2,3-dihydroxy(1,2,3-^1^3C₃)propoxy]phosphonic acid; cyclohexanamine
• IUPAC Traditional name: 2,3-dihydroxy(1,2,3-^1^3C₃)propoxyphosphonic acid; cyclohexylamine
• Synonyms: 1,2,3-Propanetriol-13C3 1-(Dihydrogen Phosphate) Cyclohexanamine; Sα-Glycerophosphate-13C3 Cyclohexylamine Salt; Glycerol-13C3 3-Phosphate Dicyclohexylammonium Salt; α-Glycerophosphoric Acid-13C3 Bis-cyclohexylammonium Salt

Database IDs

• PubChem SID: 162263863
• PubChem CID: 71317129

CALCULATED PROPERTIES

• LogD (pH = 5.5): -4.366909
• LogD (pH = 7.4): -5.247459
• Log P: -1.9625801
• Molar Refractivity: 31.389 cm^3
• Polarizability: 12.865609 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 1.5077547
• H Acceptors: 5
• H Donor: 4

DETAILS

Toronto Research Chemicals - G598752

Labelled Glycerol 3-phosphate (G598750). It is produced from Glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in brain and skeleta

REFERENCES

• Kalhan, C., et al.: Clin. Perinatol., 27, 23 (2000)
• Conlon, C., et al.: Anal. Biochem., 311, 191 (2000)
• Rigo, J., et al.: J. Pediatr., 149, S80 (2000)