(R)-8-hydroxy-5-(1-hydroxy-2-((4-hydroxybutyl)amino)ethyl)quinolin-2(1H)-one

ID: ALA5201712

PubChem CID: 166177238

Max Phase: Preclinical

Molecular Formula: C15H20N2O4

Molecular Weight: 292.34

Names and Identifiers

Canonical SMILES:  O=c1ccc2c([C@@H](O)CNCCCCO)ccc(O)c2[nH]1

Standard InChI:  InChI=1S/C15H20N2O4/c18-8-2-1-7-16-9-13(20)10-3-5-12(19)15-11(10)4-6-14(21)17-15/h3-6,13,16,18-20H,1-2,7-9H2,(H,17,21)/t13-/m0/s1

Standard InChI Key:  LAXUZKBMSNSUBP-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.8584    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320   -0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -0.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193    0.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025   -0.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141   -1.0330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120   -1.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146    1.4433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1439    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  5 11  1  0
  9 12  2  0
  2 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5201712

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 292.34

Molecular Weight (Monoisotopic): 292.1423

AlogP: 0.63

#Rotatable Bonds: 7

Polar Surface Area: 105.58

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.48

CX Basic pKa: 9.47

CX LogP: -0.77

CX LogD: -1.66

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: 0.54

References

1. Carzaniga L, Linney ID, Rizzi A, Delcanale M, Schmidt W, Knight CK, Pastore F, Miglietta D, Carnini C, Cesari N, Riccardi B, Mileo V, Venturi L, Moretti E, Blackaby WP, Patacchini R, Accetta A, Biagetti M, Bassani F, Tondelli M, Murgo A, Battipaglia L, Villetti G, Puccini P, Catinella S, Civelli M, Rancati F..  (2022)  Discovery of Clinical Candidate CHF-6366: A Novel Super-soft Dual Pharmacology Muscarinic Antagonist and β₂ Agonist (MABA) for the Inhaled Treatment of Respiratory Diseases.,  65  (15.0): [PMID:35901125] [10.1021/acs.jmedchem.2c00609]

Source

Source(1):

• Scientific Literature