(2S)-2-[3-(aminomethyl)phenyl]-3-{[(1R)-1-benzenesulfonamido-2-methylpropyl](hydroxy)phosphoryl}propanoic acid

• ChemBase ID: 4575
• Molecular Formular: C20H27N2O6PS
• Molecular Mass: 454.476941
• Monoisotopic Mass: 454.13274422
• SMILES: c1ccccc1S(=O)(=O)N[C@@H](C(C)C)[P@](=O)(O)C[C@H](C(=O)O)c1cc(ccc1)CN
• Canonical SMILES: NCc1cccc(c1)[C@@H](C(=O)O)C[P@](=O)([C@H](C(C)C)NS(=O)(=O)c1ccccc1)O
• InChI: InChI=1S/C20H27N2O6PS/c1-14(2)19(22-30(27,28)17-9-4-3-5-10-17)29(25,26)13-18(20(23)24)16-8-6-7-15(11-16)12-21/h3-11,14,18-19,22H,12-13,21H2,1-2H3,(H,23,24)(H,25,26)/t18-,19+/m0/s1
• InChIKey: FNZHLCNFXRRIIC-RBUKOAKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[3-(aminomethyl)phenyl]-3-{[(1R)-1-benzenesulfonamido-2-methylpropyl](hydroxy)phosphoryl}propanoic acid
• IUPAC Traditional name: (2S)-2-[3-(aminomethyl)phenyl]-3-[(1R)-1-benzenesulfonamido-2-methylpropyl(hydroxy)phosphoryl]propanoic acid
• Synonyms: (2S)-2-[3-(AMINOMETHYL)PHENYL]-3-[(R)-HYDROXY{(1R)-2-METHYL-1-[(PHENYLSULFONYL)AMINO]PROPYL}PHOSPHORYL]PROPANOIC ACID

Database IDs

• PubChem SID: 99443392; 160968007
• PubChem CID: 23653508

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.5143558
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.2000244
• LogD (pH = 7.4): -2.8158596
• Log P: 0.550958
• Molar Refractivity: 114.4678 cm^3
• Polarizability: 45.747578 Å^3
• Polar Surface Area: 146.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.63
• LOG S: -2.68
• Solubility (Water): 9.39e-01 g/l

DETAILS

DrugBank - DB06921

Drug information: experimental