(R)-8-hydroxy-5-(1-hydroxy-2-(3-methoxy-4-(3-phenylpropoxy)phenethylamino)ethyl)quinolin-2(1H)-one

ID: ALA3800400

PubChem CID: 102262219

Max Phase: Preclinical

Molecular Formula: C29H32N2O5

Molecular Weight: 488.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCNC[C@H](O)c2ccc(O)c3[nH]c(=O)ccc23)ccc1OCCCc1ccccc1

Standard InChI:  InChI=1S/C29H32N2O5/c1-35-27-18-21(9-13-26(27)36-17-5-8-20-6-3-2-4-7-20)15-16-30-19-25(33)22-10-12-24(32)29-23(22)11-14-28(34)31-29/h2-4,6-7,9-14,18,25,30,32-33H,5,8,15-17,19H2,1H3,(H,31,34)/t25-/m0/s1

Standard InChI Key:  PNROEQYQIZJINW-VWLOTQADSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -3.5964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -3.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022   -5.2520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2960   -6.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -7.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5923   -8.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924   -9.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915  -10.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1905   -9.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904   -8.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8914   -7.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4886   -7.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4869   -6.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4888  -10.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4867  -12.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7850  -12.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7829  -14.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0812  -15.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0813  -16.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3803  -17.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6794  -16.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6793  -15.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3803  -14.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  7 11  1  0
  1 12  2  0
 10 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  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 23 25  1  0
 25 26  1  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800400

   8-hydroxy-5-[(1R)-1-hydroxy-2-[2-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethylamino]ethyl]-1H-quinolin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 488.58

Molecular Weight (Monoisotopic): 488.2311

AlogP: 4.12

#Rotatable Bonds: 12

Polar Surface Area: 103.81

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.51

CX Basic pKa: 9.65

CX LogP: 3.42

CX LogD: 2.48

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: 0.08

References

1. Weichert D, Stanek M, Hübner H, Gmeiner P..  (2016)  Structure-guided development of dual β2 adrenergic/dopamine D2 receptor agonists.,  24  (12): [PMID:27132867] [10.1016/j.bmc.2016.04.028]

Source

Source(1):

• Scientific Literature