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

• ChemBase ID: 159538
• Molecular Formular: C28H28O3
• Molecular Mass: 412.52012
• Monoisotopic Mass: 412.20384476
• SMILES: C12(C[C@H]3C[C@@H](C1)C[C@H](C2)C3)c1cc(ccc1OC)c1ccc2c(c1)ccc(c2)C(=O)O
• Canonical SMILES: COc1ccc(cc1C12C[C@@H]3C[C@@H](C2)C[C@H](C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
• InChI: InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)/t17-,18+,19-,28?
• InChIKey: LZCDAPDGXCYOEH-UGQIIZBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{4-methoxy-3-[(3R,5S,7s)-adamantan-1-yl]phenyl}naphthalene-2-carboxylic acid
• IUPAC Traditional name: adapaleno [inn-spanish]
• Synonyms: 6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic Acid; 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic Acid; CD-271; Differin; Adapalene

Database IDs

• CAS Number: 106685-40-9
• PubChem SID: 162253673
• PubChem CID: 60164

CALCULATED PROPERTIES

• Acid pKa: 3.9892612
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.938707
• LogD (pH = 7.4): 3.2933044
• Log P: 6.4585013
• Molar Refractivity: 122.0719 cm^3
• Polarizability: 49.86113 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 319-322°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A225000

Retinoid selective for retinoic acid receptor (RAR) subtypes β and γ. Antiacne.

REFERENCES

• Griffiths, C.E.M., et al.: J. Invest. Dermatol., 101, 325 (1993)
• Bernard, B.A., et al.: Skin Pharmacol., 6, 61 (1993)
• Waugh, J., et al.: Drugs, 64, 1465 (1993)