(2R,3S)-2-amino-3-(phosphonooxy)butanoic acid

• ChemBase ID: 2216
• Molecular Formular: C4H10NO6P
• Molecular Mass: 199.099061
• Monoisotopic Mass: 199.02457368
• SMILES: C[C@H](OP(=O)(O)O)[C@@H](N)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]([C@@H](OP(=O)(O)O)C)N
• InChI: InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m0/s1
• InChIKey: USRGIUJOYOXOQJ-STHAYSLISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-amino-3-(phosphonooxy)butanoic acid
• IUPAC Traditional name: phosphonothreonine
• Synonyms: D-Threonine Dihydrogen Phosphate(ester); D-O-Phosphothreonine; D-O-Phospho Threonine; Phosphonothreonine

Database IDs

• CAS Number: 96193-69-0
• PubChem SID: 46506053; 160965669
• PubChem CID: 10976469

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2107285
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.609686
• LogD (pH = 7.4): -6.9265065
• Log P: -2.7024999
• Molar Refractivity: 37.3327 cm^3
• Polarizability: 15.472433 Å^3
• Polar Surface Area: 130.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.86
• LOG S: -0.93
• Solubility (Water): 2.35e+01 g/l

DETAILS

DrugBank - DB02482

• Drug Groups: experimental
• Description: The phosphoric acid ester of threonine. Used as an identifier in the analysis of peptides, proteins, and enzymes. [PubChem]

Toronto Research Chemicals - P364500

The D enantiomer of Threonine derivative. Phosphothreonine phosphatase stereoselectivity.

REFERENCES

• Scollar, M.P., et al.: Biotechnol. Bioengineering, 27, 247 (1985)