adamantan-1-yl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate

• ChemBase ID: 159542
• Molecular Formular: C24H27NO4
• Molecular Mass: 393.47548
• Monoisotopic Mass: 393.19400835
• SMILES: C12(CC3CC(C1)CC(C2)C3)OC(=O)c1ccc(cc1)NCc1c(ccc(c1)O)O
• Canonical SMILES: Oc1ccc(c(c1)CNc1ccc(cc1)C(=O)OC12CC3CC(C2)CC(C1)C3)O
• InChI: InChI=1S/C24H27NO4/c26-21-5-6-22(27)19(10-21)14-25-20-3-1-18(2-4-20)23(28)29-24-11-15-7-16(12-24)9-17(8-15)13-24/h1-6,10,15-17,25-27H,7-9,11-14H2
• InChIKey: YJZSUCFGHXQWDM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: adamantan-1-yl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate
• IUPAC Traditional name: adamantan-1-yl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate
• Synonyms: 4-[[(2,5-Dihydroxyphenyl)methyl]amino]benzoic Acid Tricyclo[3.3.1.13,7]dec-1-yl Ester; NSC 680410; Adaphostin

Database IDs

• CAS Number: 241127-58-2
• PubChem SID: 162253677
• PubChem CID: 387042

CALCULATED PROPERTIES

• Acid pKa: 9.4588995
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.657948
• LogD (pH = 7.4): 4.6544914
• Log P: 4.65825
• Molar Refractivity: 112.4683 cm^3
• Polarizability: 42.91471 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A225020

Novel antitumor agent that induces apoptosis in tumor cells through inhibition of the tyrosine kinase BCR/ABL.

REFERENCES

• Fer, N., et al.: J. Exp. Clin. Cancer Res., 29, 91 (2010)
• Long, J., et al.: Cancer Chemother. Pharmacol. 59, 527 (2010)
• Mukhopadhyay, I., et al.: J. Biol. Chem. 281, 37330 (2010)