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

• ChemBase ID: 154819
• Molecular Formular: C28H28O3
• Molecular Mass: 412.52012
• Monoisotopic Mass: 412.20384476
• SMILES: COc1c(cc(cc1)c1cc2c(cc(cc2)C(=O)O)cc1)[C@@]12C[C@H]3C[C@@H](C1)C[C@H](C2)C3
• Canonical SMILES: COc1ccc(cc1[C@]12C[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-AADAIPAGSA-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
• MDL Number: MFCD03106112
• PubChem SID: 162248957
• 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: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C28H28O3

DETAILS

Sigma Aldrich - A7486

Application
Adapalene, a retinoic acid analogue, is a RARβ and RARγ agonist. Adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Adapalene gel is an efficacious treatment for acne vulgaris.
Biochem/physiol Actions
Retinoic acid analogue that is a RARβ and RARγ agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARα and RXRα receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Displays comedolytic activity. Its unique pharmacological properties make it superior to other retinoids for the treatment of acne.