(2S)-2-amino-3-{[hydroxy(propan-2-yloxy)phosphoryl]oxy}propanoic acid

• ChemBase ID: 1575
• Molecular Formular: C6H14NO6P
• Molecular Mass: 227.152221
• Monoisotopic Mass: 227.0558738
• SMILES: CC(C)O[P@@](=O)(O)OC[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CO[P@@](=O)(OC(C)C)O
• InChI: InChI=1S/C6H14NO6P/c1-4(2)13-14(10,11)12-3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)(H,10,11)/t5-/m0/s1
• InChIKey: DALHHSOTZKMXMV-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{[hydroxy(propan-2-yloxy)phosphoryl]oxy}propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{[hydroxy(isopropoxy)phosphoryl]oxy}propanoic acid
• Synonyms: Monoisopropylphosphorylserine

Database IDs

• PubChem SID: 160965032; 46504829
• PubChem CID: 46936220; 17754078

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6659602
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.712598
• LogD (pH = 7.4): -5.2280164
• Log P: -2.0502126
• Molar Refractivity: 46.5636 cm^3
• Polarizability: 19.265656 Å^3
• Polar Surface Area: 119.08 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.58
• LOG S: -0.93
• Solubility (Water): 2.68e+01 g/l

DETAILS

DrugBank - DB01805

Drug information: experimental