methyl (6S,7S)-7-(hydroxycarbamoyl)-6-(4-phenylpiperazine-1-carbonyl)-5-azaspiro[2.5]octane-5-carboxylate

• ChemBase ID: 159576
• Molecular Formular: C21H28N4O5
• Molecular Mass: 416.47082
• Monoisotopic Mass: 416.20597002
• SMILES: [C@@H]1(N(CC2(C[C@@H]1C(=O)NO)CC2)C(=O)OC)C(=O)N1CCN(CC1)c1ccccc1
• Canonical SMILES: ONC(=O)[C@H]1CC2(CC2)CN([C@@H]1C(=O)N1CCN(CC1)c1ccccc1)C(=O)OC
• InChI: InChI=1S/C21H28N4O5/c1-30-20(28)25-14-21(7-8-21)13-16(18(26)22-29)17(25)19(27)24-11-9-23(10-12-24)15-5-3-2-4-6-15/h2-6,16-17,29H,7-14H2,1H3,(H,22,26)/t16-,17-/m0/s1
• InChIKey: DJXMSZSZEIKLQZ-IRXDYDNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (6S,7S)-7-(hydroxycarbamoyl)-6-(4-phenylpiperazine-1-carbonyl)-5-azaspiro[2.5]octane-5-carboxylate
• IUPAC Traditional name: methyl (6S,7S)-7-(hydroxycarbamoyl)-6-(4-phenylpiperazine-1-carbonyl)-5-azaspiro[2.5]octane-5-carboxylate
• Synonyms: (6S,7S)-7-[(Hydroxyamino)carbonyl]-6-[(4-phenyl-1-piperazinyl)carbonyl]-5-azaspiro[2.5]octane-5-carboxylic Acid Methyl Ester; INCB 007839; Aderbasib

Database IDs

• CAS Number: 791828-58-5
• PubChem SID: 162253711
• PubChem CID: 16070111

CALCULATED PROPERTIES

• Acid pKa: 8.851051
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.7992476
• LogD (pH = 7.4): 0.78800523
• Log P: 0.8030854
• Molar Refractivity: 108.7592 cm^3
• Polarizability: 41.932076 Å^3
• Polar Surface Area: 102.42 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A291560

Aderbasib is a azaspiro[2.5]octanehydroxamide derivative as inhibitor of metalloproteases for the treatment of disorders such as cancer, arthritis, cardiovascular or skin disorders.

REFERENCES

• Kuipers, W., et al.: J. Med. Chem., 38, 1942 (1995)
• Molina, M.A., et al.: Clin. Cancer Res., 8, 347 (1995)
• Moss, M.L., et al.: Biochemistry, 43, 7227 (1995)