4-[(5,5,8,8-tetramethyl-6-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid

• ChemBase ID: 172122
• Molecular Formular: C22H23NO4
• Molecular Mass: 365.42232
• Monoisotopic Mass: 365.16270822
• SMILES: C1C(=O)C(c2c(C1(C)C)cc(cc2)NC(=O)c1ccc(cc1)C(=O)O)(C)C
• Canonical SMILES: O=C1CC(C)(C)c2c(C1(C)C)ccc(c2)NC(=O)c1ccc(cc1)C(=O)O
• InChI: InChI=1S/C22H23NO4/c1-21(2)12-18(24)22(3,4)16-10-9-15(11-17(16)21)23-19(25)13-5-7-14(8-6-13)20(26)27/h5-11H,12H2,1-4H3,(H,23,25)(H,26,27)
• InChIKey: HKWXTAAIQIWIKN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(5,5,8,8-tetramethyl-6-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid
• IUPAC Traditional name: 4-[(5,5,8,8-tetramethyl-6-oxo-7H-naphthalen-2-yl)carbamoyl]benzoic acid
• Synonyms: 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-6-oxo-2-naphthalenyl)amino]carbonyl]benzoic Acid; Keto Tamibarotene

Database IDs

• CAS Number: 162661-91-8
• PubChem SID: 164228032
• PubChem CID: 29982685

CALCULATED PROPERTIES

• Acid pKa: 3.6937819
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.8770027
• LogD (pH = 7.4): 1.3738389
• Log P: 4.6818166
• Molar Refractivity: 105.0705 cm^3
• Polarizability: 39.329712 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K285000

The major metabolite of Tamibarotene.

REFERENCES

• Hashimoto, S., et al.: Xenobiotica, 24, 1177 (1994)