8-hydroxy-5-[(1S,2R)-1-hydroxy-2-[(propan-2-yl)amino]butyl]-1,2-dihydroquinolin-2-one hydrochloride

• ChemBase ID: 176182
• Molecular Formular: C16H23ClN2O3
• Molecular Mass: 326.81842
• Monoisotopic Mass: 326.13972029
• SMILES: c1cc(c2c(c1O)[nH]c(=O)cc2)[C@H](O)[C@@H](CC)NC(C)C.Cl
• Canonical SMILES: CC[C@H]([C@H](c1ccc(c2c1ccc(=O)[nH]2)O)O)NC(C)C.Cl
• InChI: InChI=1S/C16H22N2O3.ClH/c1-4-12(17-9(2)3)16(21)11-5-7-13(19)15-10(11)6-8-14(20)18-15;/h5-9,12,16-17,19,21H,4H2,1-3H3,(H,18,20);1H/t12-,16+;/m1./s1
• InChIKey: AEQDBKHAAWUCMT-KKJWGQAZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-hydroxy-5-[(1S,2R)-1-hydroxy-2-[(propan-2-yl)amino]butyl]-1,2-dihydroquinolin-2-one hydrochloride
• IUPAC Traditional name: 8-hydroxy-5-[(1S,2R)-1-hydroxy-2-(isopropylamino)butyl]-1H-quinolin-2-one hydrochloride
• Synonyms: rel-8-Hydroxy-5-[(1R,2S)-1-hydroxy-2-[(1-methylethyl)amino]butyl]-2(1H)-quinolinone Hydrochloride, Hydrate; R*,S*)-(+/-)-8-Hydroxy-5-[1-hydroxy-2-[(1-methylethyl)amino]butyl]-2(1H)-quinolinone Monohydrochloride, Hydrate; Procaterol Hydrochloride Hemihydrate

Database IDs

• CAS Number: 81262-93-3
• PubChem SID: 164232092
• PubChem CID: 16219912

CALCULATED PROPERTIES

• Acid pKa: 8.519182
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.2235061
• LogD (pH = 7.4): -0.0811332
• Log P: 0.88412946
• Molar Refractivity: 84.5808 cm^3
• Polarizability: 31.786533 Å^3
• Polar Surface Area: 81.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P155490

Short-acting β2-adrenergic receptor agonist used to treat asthma.

REFERENCES

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)
• Yalcin, I., et al.: Exper. Neurol., 221, 115 (2009)