(1R,2S)-2-[(3,5-dichlorophenyl)carbamoyl]cyclohexane-1-carboxylic acid

• ChemBase ID: 154138
• Molecular Formular: C14H15Cl2NO3
• Molecular Mass: 316.1798
• Monoisotopic Mass: 315.04289871
• SMILES: c1c(cc(cc1Cl)Cl)NC(=O)[C@H]1CCCC[C@H]1C(=O)O
• Canonical SMILES: O=C([C@H]1CCCC[C@H]1C(=O)O)Nc1cc(Cl)cc(c1)Cl
• InChI: InChI=1S/C14H15Cl2NO3/c15-8-5-9(16)7-10(6-8)17-13(18)11-3-1-2-4-12(11)14(19)20/h5-7,11-12H,1-4H2,(H,17,18)(H,19,20)/t11-,12+/m0/s1
• InChIKey: VSMUYYFJVFSVCA-NWDGAFQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-[(3,5-dichlorophenyl)carbamoyl]cyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1R,2S)-2-[(3,5-dichlorophenyl)carbamoyl]cyclohexane-1-carboxylic acid
• Synonyms: (±)-cis-2-(3,5-Dicholorphenylcarbamoyl)cyclohexanecarboxylic acid; VU0155041

Database IDs

• MDL Number: MFCD03544581
• PubChem SID: 162248277
• PubChem CID: 888023

CALCULATED PROPERTIES

• Acid pKa: 3.913924
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.1630151
• LogD (pH = 7.4): 0.54895
• Log P: 3.7552922
• Molar Refractivity: 77.9727 cm^3
• Polarizability: 29.89485 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble54 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H15Cl2NO3

DETAILS

Sigma Aldrich - V1640

Biochem/physiol Actions
VU0155041 is a mixed allosteric agonist/positive allosteric modulator (PAM) of mGluR4. VU0155041 is approximately 8-fold more potent than PHCCC and does not show any significant potentiator or antagonist activity at other mGluR subtypes. It is soluble in an aqueous vehicle and intracerebroventricular administration of 31-316 nmol of VU0155041 dose-dependently decreased haloperidol-induced catalepsy and reserpine-induced akinesia in rats. VU0155041 exhibits selectivity for mGluR4 relative to 67 different targets and does not affect the function of striatal NMDA receptors.
VU0155041 is a positive allosteric modulator of the metabotropic glutamate receptor subtype 4. It also shows some direct agonist activity, but at a site different from the glutamate binding site. /VU0155041 is approximately 8-fold more potent than PHCCC and enhances the activity of glutamate also about 8-fold. It shows promising anti-Parkinsonian effects in animal models of Parkinson′s disease.