3-(3-{2-[(4Z)-1-(3,4-dimethylphenyl)-3-(13C)methyl-5-oxo-4,5-dihydro(3,4,5-13C3)-1H-pyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid

• ChemBase ID: 167972
• Molecular Formular: C25H22N4O4
• Molecular Mass: 446.43719935
• Monoisotopic Mass: 446.17752456
• SMILES: c1(cc(ccc1C)N1N=[13C](/[13C](=N/Nc2cccc(c2O)c2cc(ccc2)C(=O)O)/[13C]1=O)[13CH3])C
• Canonical SMILES: OC(=O)c1cccc(c1)c1cccc(c1O)N/N=[13C]\1/[13C](=NN([13C]1=O)c1ccc(c(c1)C)C)[13CH3]
• InChI: InChI=1S/C25H22N4O4/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33/h4-13,26,30H,1-3H3,(H,32,33)/b27-22-/i3+1,16+1,22+1,24+1
• InChIKey: XDXWLKQMMKQXPV-PHYJMDTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-{2-[(4Z)-1-(3,4-dimethylphenyl)-3-(^1^3C)methyl-5-oxo-4,5-dihydro(3,4,5-^1^3C₃)-1H-pyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid
• IUPAC Traditional name: 3-(3-{2-[(4Z)-1-(3,4-dimethylphenyl)-3-(^1^3C)methyl-5-oxo(3,4,5-^1^3C₃)pyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid
• Synonyms: 3'-[2-[(2Z)-1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid-13C4; SB 497115-13C4; Eltrombopag-13C4

Database IDs

• PubChem SID: 162262105
• PubChem CID: 46781446

CALCULATED PROPERTIES

• Acid pKa: 3.987072
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 4.5041695
• LogD (pH = 7.4): 2.8513787
• Log P: 6.0262365
• Molar Refractivity: 126.4827 cm^3
• Polarizability: 47.734787 Å^3
• Polar Surface Area: 114.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E508002

An agonist of the Thrombopoietin (Tpo) receptor, used as treatment for thrombocytopenia

REFERENCES

• Bussel, J., et al.: New Eng. J. Med., 357, 2237 (2007)
• Marsilje, T., et al.: Bioorg. Med. Chem. Lett., 18, 5259 (2007)
• Alper, P., et al.: Bioorg. Med. Chem. Lett., 18, 5255 (2007)