6-{4-methoxy-3-[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]phenyl}naphthalene-2-carboxylic acid

• ChemBase ID: 170088
• Molecular Formular: C28H28O4
• Molecular Mass: 428.51952
• Monoisotopic Mass: 428.19875938
• SMILES: [C@]12(C[C@H]3C[C@@](C1)(C[C@H](C2)C3)O)c1cc(ccc1OC)c1ccc2c(c1)ccc(c2)C(=O)O
• Canonical SMILES: COc1ccc(cc1[C@]12C[C@@H]3C[C@@H](C1)C[C@](C2)(C3)O)c1ccc2c(c1)ccc(c2)C(=O)O
• InChI: InChI=1S/C28H28O4/c1-32-25-7-6-22(20-2-3-21-10-23(26(29)30)5-4-19(21)9-20)11-24(25)27-12-17-8-18(13-27)15-28(31,14-17)16-27/h2-7,9-11,17-18,31H,8,12-16H2,1H3,(H,29,30)/t17-,18+,27+,28-
• InChIKey: ZVFMDETWRVTMJF-GZDATYFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{4-methoxy-3-[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]phenyl}naphthalene-2-carboxylic acid
• IUPAC Traditional name: 6-{4-methoxy-3-[(1r,3s,5R,7S)-3-hydroxyadamantan-1-yl]phenyl}naphthalene-2-carboxylic acid
• Synonyms: Hydroxy Adapalene

Database IDs

• PubChem SID: 164225998
• PubChem CID: 71748803

CALCULATED PROPERTIES

• Acid pKa: 3.9892612
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6234996
• LogD (pH = 7.4): 1.9780971
• Log P: 5.1432943
• Molar Refractivity: 123.754 cm^3
• Polarizability: 50.43572 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H750045

A potential metabolite of Adapalene (A225000).