2-(3-{1-[2-(3,4-dichlorophenyl)-N-methylacetamido]-2-(pyrrolidin-1-yl)ethyl}phenoxy)acetic acid hydrochloride

• ChemBase ID: 112274
• Molecular Formular: C23H27Cl3N2O4
• Molecular Mass: 501.83048
• Monoisotopic Mass: 500.10364039
• SMILES: Cl.CN(C(CN1CCCC1)c1cc(OCC(=O)O)ccc1)C(=O)Cc1ccc(Cl)c(Cl)c1
• Canonical SMILES: OC(=O)COc1cccc(c1)C(N(C(=O)Cc1ccc(c(c1)Cl)Cl)C)CN1CCCC1.Cl
• InChI: InChI=1S/C23H26Cl2N2O4.ClH/c1-26(22(28)12-16-7-8-19(24)20(25)11-16)21(14-27-9-2-3-10-27)17-5-4-6-18(13-17)31-15-23(29)30;/h4-8,11,13,21H,2-3,9-10,12,14-15H2,1H3,(H,29,30);1H
• InChIKey: FNDGLVOYAQNQPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-{1-[2-(3,4-dichlorophenyl)-N-methylacetamido]-2-(pyrrolidin-1-yl)ethyl}phenoxy)acetic acid hydrochloride
• IUPAC Traditional name: 3-{1-[2-(3,4-dichlorophenyl)-N-methylacetamido]-2-(pyrrolidin-1-yl)ethyl}phenoxyacetic acid hydrochloride
• Synonyms: 4,4'-(2-ACETYL-1,3-GLYCEROL) BISANHYDRO MELLITATE; (±)-1-[2,3-(Dihydro-7-methyl-1H-inden-4-yl)oxy]-3-[(1-methylethyl)amino]-2-butanol hydrochloride; R,S-[3-[1-[[(3,4-Dichlorophenyl)acetyl]methylamino]-2-(1-pyrrolidinyl)ethyl] phenoxy]-acetic acid hydrochloride; ICI 204,448 hydrochloride

Database IDs

• CAS Number: 121264-04-8
• MDL Number: MFCD00153814
• PubChem SID: 162097228; 24278040
• PubChem CID: 129407

CALCULATED PROPERTIES

• Acid pKa: 3.1956012
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.2569684
• LogD (pH = 7.4): 1.2211864
• Log P: 1.2570902
• Molar Refractivity: 120.9815 cm^3
• Polarizability: 47.1759 Å^3
• Polar Surface Area: 70.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble12 mg/mL; dilute sodium carbonate: soluble4 mg/mL; H2O: soluble4.5 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... OPRK1(4986)

DETAILS

MP Biomedicals - 05223251

MP Biomedicals Rare Chemical collection

Sigma Aldrich - I122

Biochem/physiol Actions
κ opioid receptor agonist that does not cross the blood-brain barrier.