6-[3-(adamantan-1-yl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid

• ChemBase ID: 154244
• Molecular Formular: C27H26O3
• Molecular Mass: 398.49354
• Monoisotopic Mass: 398.18819469
• SMILES: c1cc(cc2c1cc(cc2)C(=O)O)c1ccc(c(c1)C12CC3CC(C1)CC(C3)C2)O
• Canonical SMILES: Oc1ccc(cc1C12CC3CC(C2)CC(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)
• InChIKey: LDGIHZJOIQSHPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[3-(adamantan-1-yl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
• IUPAC Traditional name: 6-[3-(adamantan-1-yl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
• Synonyms: 6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid; AHPN; CD437

Database IDs

• CAS Number: 125316-60-1
• MDL Number: MFCD03106506
• PubChem SID: 24724445; 162248383
• 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: >10 mg/mL; H2O: insoluble
• Apperance: yellow solid
• Melting Point: 271.6-276 °C

Safety Information

• RTECS: QJ1975900
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... RARA(5914), RARB(5915), RARG(5916)

Product Information

• Purity: ≥98% (HPLC)
• Impurities: ~0.5 mol/mol water
• Empirical Formula (Hill Notation): C27H26O3

DETAILS

Sigma Aldrich - C5865

Biochem/physiol Actions
CD437 is a retinoic acid receptor (RAR)γ-selective agonist, γ-selective retinoid; potent inducer of apoptosis.