(2S)-2-[(2S)-2-amino-3-(phosphonooxy)propanamido]-3-(phosphonooxy)propanoic acid

• ChemBase ID: 176691
• Molecular Formular: C6H14N2O11P2
• Molecular Mass: 352.129682
• Monoisotopic Mass: 352.00728254
• SMILES: N(C(=O)[C@H](COP(=O)(O)O)N)[C@@H](COP(=O)(O)O)C(=O)O
• Canonical SMILES: O=C([C@H](COP(=O)(O)O)N)N[C@H](C(=O)O)COP(=O)(O)O
• InChI: InChI=1S/C6H14N2O11P2/c7-3(1-18-20(12,13)14)5(9)8-4(6(10)11)2-19-21(15,16)17/h3-4H,1-2,7H2,(H,8,9)(H,10,11)(H2,12,13,14)(H2,15,16,17)/t3-,4-/m0/s1
• InChIKey: PNAYBQVLHUSEEO-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-amino-3-(phosphonooxy)propanamido]-3-(phosphonooxy)propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-amino-3-(phosphonooxy)propanamido]-3-(phosphonooxy)propanoic acid
• Synonyms: O-Phosphono-L-seryl-O-phosphono-L-serine; N-(O-Phosphono-L-seryl)-L-serine Dihydrogen Phosphate (Ester); N-L-Seryl-L-serine Bis(dihydrogen phosphate); PN: WO2010142041 SEQID: 15 claimed protein; 21: PN: WO03093314 PAGE: 45 claimed protein; Phosphoserylphosphoserine; Phosphoseryl Phosphoserine

Database IDs

• CAS Number: 1492-21-3
• PubChem SID: 164232601
• PubChem CID: 13875176

CALCULATED PROPERTIES

• Acid pKa: 1.0395385
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -9.123779
• LogD (pH = 7.4): -12.365374
• Log P: -4.8307967
• Molar Refractivity: 62.6279 cm^3
• Polarizability: 25.822258 Å^3
• Polar Surface Area: 225.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P362000

Phosphoseryl Phosphoserine is a a partial analogue of human salivary statherin, a protein inhibitor of calcium phosphate precipitation in human saliva.

REFERENCES

• Schlesinger, D.H. et al.: Int. J. Pep. Protein Res., 30, 257 (1987)
• Hay, D.I. et al.: Calc. Tiss. Int., 40, 126 (1987)