2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol

• ChemBase ID: 153677
• Molecular Formular: C24H40O3
• Molecular Mass: 376.5726
• Monoisotopic Mass: 376.29774514
• SMILES: CCCCCCC(C)(C)c1ccc(c(c1)O)[C@@H]1C[C@@H](CC[C@H]1CCCO)O
• Canonical SMILES: CCCCCCC(c1ccc(c(c1)O)[C@@H]1C[C@H](O)CC[C@H]1CCCO)(C)C
• InChI: InChI=1S/C24H40O3/c1-4-5-6-7-14-24(2,3)19-11-13-21(23(27)16-19)22-17-20(26)12-10-18(22)9-8-15-25/h11,13,16,18,20,22,25-27H,4-10,12,14-15,17H2,1-3H3/t18-,20-,22-/m1/s1
• InChIKey: YNZFFALZMRAPHQ-SYYKKAFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol
• IUPAC Traditional name: 2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol
• Synonyms: 5-(1,1-Dimethylheptyl)-2-[5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]phenol; CP-55940; (3S)-3-[3-(1-Carboxy-1-methylethoxy)phenyl]-1-piperidinecarboxylic Acid 1-[[4-(1-Methylethyl)phenyl]methyl] Ester; (S)-3-[3-(1-Carboxy-1-methylethoxy)phenyl]piperidine-1-carboxylic Acid 4-Isopropylbenzyl Ester; CP 868388; CP-868388

Database IDs

• CAS Number: 702681-67-2; 83002-04-4
• MDL Number: MFCD00673965
• PubChem SID: 162247816; 24278295
• PubChem CID: 104895

CALCULATED PROPERTIES

• Lipinski's Rule of Five: false
• Acid pKa: 10.465278
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 5.905324
• LogD (pH = 7.4): 5.9049573
• Log P: 5.9053288
• Molar Refractivity: 113.2502 cm^3
• Polarizability: 44.443966 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 10

PROPERTIES

Physical Property

• Solubility: DMSO: soluble15 mg/mL; H2O: slightly soluble
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CNR1(1268), CNR2(1269)rat ... Cnr1(25248)

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C24H40O3

DETAILS

Sigma Aldrich - C1112

Biochem/physiol Actions
CP-55940 is a selective cannabinoid receptor agonist.

Toronto Research Chemicals - C781400

CP-868388 is a potent PPARα agonist with a Ki of 10.8 nM for therapeutic use as hypolipemics, antidiabetics.

REFERENCES

• Komoto, T., et al.: Chem. Pharm. Bull., 48, 1978 (2000)
• Anderson, S., et al.: J. Biol. Chem., 279, 52390 (2000)
• Cariello, N., et al.: Toxicol. Sci., 88, 250 (2000)