(S)-4-(1-Hydroxy-2-((3-methoxy-4-(3-phenylpropoxy)phenethyl)amino)ethyl)benzene-1,2-diol

ID: ALA3799427

PubChem CID: 127046951

Max Phase: Preclinical

Molecular Formula: C26H31NO5

Molecular Weight: 437.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCNC[C@@H](O)c2ccc(O)c(O)c2)ccc1OCCCc1ccccc1

Standard InChI:  InChI=1S/C26H31NO5/c1-31-26-16-20(9-12-25(26)32-15-5-8-19-6-3-2-4-7-19)13-14-27-18-24(30)21-10-11-22(28)23(29)17-21/h2-4,6-7,9-12,16-17,24,27-30H,5,8,13-15,18H2,1H3/t24-/m1/s1

Standard InChI Key:  PGSGTPNUOJTSEM-XMMPIXPASA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4007    1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6971    0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6919   -0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3903   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0939   -0.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9875   -1.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9802   -3.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2758   -3.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2684   -5.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5640   -6.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5589   -7.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8553   -8.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1569   -7.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1622   -6.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8658   -5.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9979    1.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0004    2.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  1  7  1  0
  2  8  1  0
  9 10  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 21 22  1  0
 22 23  1  0
 20 21  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
 23 24  1  0
 17 20  1  0
 30 31  1  0
 16 30  1  0
 11 12  1  0
 10 11  1  0
  9 32  1  1
  4  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3799427

   ---

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: 437.54

Molecular Weight (Monoisotopic): 437.2202

AlogP: 3.98

#Rotatable Bonds: 12

Polar Surface Area: 91.18

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.80

CX Basic pKa: 8.97

CX LogP: 3.63

CX LogD: 2.39

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: 0.07

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