2-{4-[hydroxy(4-nitrophenoxy)phosphoryl]butanamido}acetic acid

• ChemBase ID: 6010
• Molecular Formular: C12H15N2O8P
• Molecular Mass: 346.229861
• Monoisotopic Mass: 346.05660208
• SMILES: c1(ccc(cc1)[N+](=O)[O-])O[P@](=O)(O)CCCC(=O)NCC(=O)O
• Canonical SMILES: O=C(NCC(=O)O)CCC[P@](=O)(Oc1ccc(cc1)[N+](=O)[O-])O
• InChI: InChI=1S/C12H15N2O8P/c15-11(13-8-12(16)17)2-1-7-23(20,21)22-10-5-3-9(4-6-10)14(18)19/h3-6H,1-2,7-8H2,(H,13,15)(H,16,17)(H,20,21)
• InChIKey: WLNKGRQBMNPVSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[hydroxy(4-nitrophenoxy)phosphoryl]butanamido}acetic acid
• IUPAC Traditional name: {4-[hydroxy(4-nitrophenoxy)phosphoryl]butanamido}acetic acid
• Synonyms: PARA-NITROPHENYLPHOSPHONOBUTANOYL-GLYCINE

Database IDs

• PubChem SID: 99444865; 160969435
• PubChem CID: 449244

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8095226
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -4.184216
• LogD (pH = 7.4): -5.7261767
• Log P: -0.06611672
• Molar Refractivity: 77.2289 cm^3
• Polarizability: 29.749474 Å^3
• Polar Surface Area: 158.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.12
• LOG S: -3.3
• Solubility (Water): 1.74e-01 g/l

DETAILS

DrugBank - DB08394

Drug information: experimental