cyclohexyl N-(3-phenylphenyl)carbamate

• ChemBase ID: 130096
• Molecular Formular: C19H21NO2
• Molecular Mass: 295.37554
• Monoisotopic Mass: 295.15722892
• SMILES: O=C(OC1CCCCC1)Nc1cccc(c1)c1ccccc1
• Canonical SMILES: O=C(Nc1cccc(c1)c1ccccc1)OC1CCCCC1
• InChI: InChI=1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21)
• InChIKey: HHVUFQYJOSFTEH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohexyl N-(3-phenylphenyl)carbamate
• IUPAC Traditional name: cyclohexyl N-(3-phenylphenyl)carbamate
• Synonyms: Biphenyl-3-yl Carbamic Acid, Cyclohexyl Ester; N-[1,1'-Biphenyl]-3-yl-carbamic Acid Cyclohexyl Ester; [1,1'-Biphenyl]-3-yl-carbamic acid; cyclohexyl ester; URB602; [1,1’-Biphenyl]-3-yl-carbamic acid cyclohexyl ester; URB602

Database IDs

• CAS Number: 565460-15-3
• MDL Number: MFCD08457914
• PubChem SID: 162224381
• PubChem CID: 10979337
• CHEMBL: 77767
• Chemspider ID: 9154538
• Wikipedia Title: URB602

CALCULATED PROPERTIES

• Acid pKa: 12.972227
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.2767434
• LogD (pH = 7.4): 5.276742
• Log P: 5.2767434
• Molar Refractivity: 88.695 cm^3
• Polarizability: 35.370617 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL
• Apperance: Crystalline solid; Off-White Solid; white to off-white powder
• Melting Point: 122-123°C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H21NO2

DETAILS

Sigma Aldrich - U3010

Biochem/physiol Actions
URB602 is an inhibitor of monoacylglycerol lipase (MGL). The IC50 = 28 μM and Km = 20 μM. URB602 increases 2-arachidonoylglycerol (2-AG) concentrations. When URB602 is injected into the periaqueductal grey matter, it enhances stress-induced analgesia (tail-flick test) in a CB1-dependent manner. An effect that is prevented by a CB1 cannabinoid receptor antagonist, Rimonabant (SR141716). URB602 is not suitable for systemic administration due to relatively low potency, but useful for research of pain and stress-related disorders, which identifies MGL as a previously unrecognized therapeutic target (highlighted in Chemical Engineering News, June 27, 2005).

Toronto Research Chemicals - U821925

URB602 is a selective inhibitor of MGL, exhibiting an IC50 of 28 μM for the rat brain enzyme. It does not inhibit fatty acid amide hydrolase (FAAH) at concentrations up to 100 μM, or other lipid metabolizing enzymes such as diacylglycerol lipase or cyclooxygenase-2.5 6 Inhibition of 2-AG hydrolysis is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.

REFERENCES

• Hohmann, A.G., et al.: Nature, 435, 1108 (2005)
• Suplita, R.L., et al.: Neuropharmacol., Nov. 25 (epub), (2005)