tripotassium (1S)-4-(3-phenoxyphenyl)-1-phosphonatobutane-1-sulfonate

• ChemBase ID: 162455
• Molecular Formular: C16H16K3O7PS
• Molecular Mass: 500.627701
• Monoisotopic Mass: 499.92655552
• SMILES: c1cccc(c1)Oc1cccc(c1)CCC[C@@H](P(=O)([O-])[O-])S(=O)(=O)[O-].[K+].[K+].[K+]
• Canonical SMILES: [O-]P(=O)([C@@H](S(=O)(=O)[O-])CCCc1cccc(c1)Oc1ccccc1)[O-].[K+].[K+].[K+]
• InChI: InChI=1S/C16H19O7PS.3K/c17-24(18,19)16(25(20,21)22)11-5-7-13-6-4-10-15(12-13)23-14-8-2-1-3-9-14;;;/h1-4,6,8-10,12,16H,5,7,11H2,(H2,17,18,19)(H,20,21,22);;;/q;3*+1/p-3/t16-;;;/m0.../s1
• InChIKey: DRADVLDMPYYQDB-OKUPDQQSSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: tripotassium (1S)-4-(3-phenoxyphenyl)-1-phosphonatobutane-1-sulfonate
• IUPAC Traditional name: tripotassium (1S)-4-(3-phenoxyphenyl)-1-phosphonatobutane-1-sulfonate
• Synonyms: (αS)-3-Phenoxy-α-phosphonobenzenebutanesulfonic Acid Tripotassium Salt; BMS 188745 Potassium Salt

Database IDs

• CAS Number: 157126-15-3
• PubChem SID: 162256590
• PubChem CID: 15784674

CALCULATED PROPERTIES

• Acid pKa: -1.1094701
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -2.332863
• LogD (pH = 7.4): -2.4187694
• Log P: 2.2690141
• Molar Refractivity: 88.7462 cm^3
• Polarizability: 36.51411 Å^3
• Polar Surface Area: 129.62 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B595900

Potassium salts of aralkylphosphonosulfonic acids are prepared as inhibitors of dehydrosqualene synthase (CrtM) in order to inhibit the biosynthesis of the Staphylococcus aureus virulence factor staphyloxanthin.

REFERENCES

• Magnin, D., et al.: J. Med. Chem., 39, 657 (1996)
• Sharma, A., et al.: J. Clin. Pharmacol., 38, 1116 (1996)
• Liu, G., et al.: J. Exp. Med., 202, 209 (1996)