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

• ChemBase ID: 166370
• Molecular Formular: C27H26O3
• Molecular Mass: 398.49354
• Monoisotopic Mass: 398.18819469
• SMILES: C12(C[C@H]3C[C@@H](C1)C[C@H](C2)C3)c1cc(ccc1O)c1ccc2c(c1)ccc(c2)C(=O)O
• Canonical SMILES: Oc1ccc(cc1C12C[C@@H]3C[C@@H](C2)C[C@H](C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
• InChI: InChI=1S/C27H26O3/c28-25-6-5-22(20-1-2-21-11-23(26(29)30)4-3-19(21)10-20)12-24(25)27-13-16-7-17(14-27)9-18(8-16)15-27/h1-6,10-12,16-18,28H,7-9,13-15H2,(H,29,30)/t16-,17+,18-,27?
• InChIKey: LDGIHZJOIQSHPB-PSAKPEQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{4-hydroxy-3-[(3R,5S,7s)-adamantan-1-yl]phenyl}naphthalene-2-carboxylic acid
• IUPAC Traditional name: 6-{4-hydroxy-3-[(3R,5S,7s)-adamantan-1-yl]phenyl}naphthalene-2-carboxylic acid
• Synonyms: 6-(4-Hydroxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic Acid; 6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalenecarboxylic Acid; AHPN; CD 437; CD 437/AHPN; O-Desmethyl Adapalene

Database IDs

• CAS Number: 125316-60-1
• PubChem SID: 162260503
• PubChem CID: 135411

CALCULATED PROPERTIES

• Acid pKa: 3.9892614
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.792808
• LogD (pH = 7.4): 3.1470335
• Log P: 6.3126073
• Molar Refractivity: 117.5896 cm^3
• Polarizability: 47.9389 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 269-273°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D290680

An intermediate in the preparation of Adapalene derivatives.

REFERENCES

• Zinner, R., et al.: Mol. Cancer Ther., 8, 521 (2009)
• Virtanen, M., et al.: Exper. Dermatol., 19, 674 (2009)