(2S)-2-amino-3-(1-phosphono-1H-imidazol-5-yl)propanoic acid

• ChemBase ID: 1667
• Molecular Formular: C6H10N3O5P
• Molecular Mass: 235.134461
• Monoisotopic Mass: 235.03580707
• SMILES: N[C@@H](Cc1cncn1P(=O)(O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1cncn1P(=O)(O)O)N
• InChI: InChI=1S/C6H10N3O5P/c7-5(6(10)11)1-4-2-8-3-9(4)15(12,13)14/h2-3,5H,1,7H2,(H,10,11)(H2,12,13,14)/t5-/m0/s1
• InChIKey: VOHVXLVXSYAFOA-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(1-phosphono-1H-imidazol-5-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-(3-phosphonoimidazol-4-yl)propanoic acid
• Synonyms: Nd1-Phosphonohistidine

Database IDs

• PubChem SID: 160965124; 46505908
• PubChem CID: 17754026; 15458487

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.55912215
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -7.103862
• LogD (pH = 7.4): -8.164594
• Log P: -6.013043
• Molar Refractivity: 49.0507 cm^3
• Polarizability: 19.389025 Å^3
• Polar Surface Area: 138.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.7
• LOG S: -2.18
• Solubility (Water): 1.79e+00 g/l

DETAILS

DrugBank - DB01899

Drug information: experimental