(S)-4-(1-Hydroxy-2-((2-(2-methoxyphenoxy)ethyl)amino)ethyl)benzene-1,2-diol

ID: ALA3799593

PubChem CID: 127047221

Max Phase: Preclinical

Molecular Formula: C17H21NO5

Molecular Weight: 319.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1OCCNC[C@@H](O)c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C17H21NO5/c1-22-16-4-2-3-5-17(16)23-9-8-18-11-15(21)12-6-7-13(19)14(20)10-12/h2-7,10,15,18-21H,8-9,11H2,1H3/t15-/m1/s1

Standard InChI Key:  AFWAVLNIGSUCHI-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 23 24  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 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4003    1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6994    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9984    1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9985    2.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6994    3.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4004    2.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7025   -0.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7426   -1.3652    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
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 14 15  1  0
 21 22  1  0
 16 21  1  0
 13 14  1  0
 11 12  1  0
 10 11  1  0
  9 23  1  1
  4  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3799593

   ---

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: 319.36

Molecular Weight (Monoisotopic): 319.1420

AlogP: 1.81

#Rotatable Bonds: 8

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: 9.40

CX Basic pKa: 8.75

CX LogP: 1.32

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.44

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