(2S,3R)-4-{[2-(3,4-dihydroxyphenyl)acetyl]oxy}-2-[(2-formylindolizin-3-yl)amino]-3-methyl-3-[(S)-sulfino]butanoic acid

• ChemBase ID: 5744
• Molecular Formular: C22H22N2O9S
• Molecular Mass: 490.48308
• Monoisotopic Mass: 490.10460129
• SMILES: O=Cc1cc2ccccn2c1N[C@@H](C(=O)O)[C@]([S@@](=O)O)(C)COC(=O)Cc1cc(c(cc1)O)O
• Canonical SMILES: O=Cc1cc2n(c1N[C@H]([C@@]([S@@](=O)O)(COC(=O)Cc1ccc(c(c1)O)O)C)C(=O)O)cccc2
• InChI: InChI=1S/C22H22N2O9S/c1-22(34(31)32,12-33-18(28)9-13-5-6-16(26)17(27)8-13)19(21(29)30)23-20-14(11-25)10-15-4-2-3-7-24(15)20/h2-8,10-11,19,23,26-27H,9,12H2,1H3,(H,29,30)(H,31,32)/t19-,22-/m0/s1
• InChIKey: DEOZLEGRVHDNKC-UGKGYDQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-4-{[2-(3,4-dihydroxyphenyl)acetyl]oxy}-2-[(2-formylindolizin-3-yl)amino]-3-methyl-3-[(S)-sulfino]butanoic acid
• IUPAC Traditional name: (2S,3R)-4-{[2-(3,4-dihydroxyphenyl)acetyl]oxy}-2-[(2-formylindolizin-3-yl)amino]-3-methyl-3-[(S)-sulfino]butanoic acid
• Synonyms: (3R)-4-{[(3,4-dihydroxyphenyl)acetyl]oxy}-N-(2-formylindolizin-3-yl)-3-sulfino-D-valine

Database IDs

• PubChem SID: 160969171; 99444587
• PubChem CID: 46937126

CALCULATED PROPERTIES

JChem

• Acid pKa: -0.36713833
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.1683495
• LogD (pH = 7.4): -3.659956
• Log P: 2.0822
• Molar Refractivity: 121.9286 cm^3
• Polarizability: 47.073223 Å^3
• Polar Surface Area: 174.87 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.77
• LOG S: -2.46
• Solubility (Water): 1.71e+00 g/l

DETAILS

DrugBank - DB08116

Drug information: experimental