(S)-5-Hydroxy-8-[1-hydroxy-2-[[3-methoxy-4-(3-phenylpropoxy)phenethyl]amino]ethyl]-2H-benzo[b][1,4]oxazin-3(4H)-one

ID: ALA3797205

PubChem CID: 127045854

Max Phase: Preclinical

Molecular Formula: C28H32N2O6

Molecular Weight: 492.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCNC[C@@H](O)c2ccc(O)c3c2OCC(=O)N3)ccc1OCCCc1ccccc1

Standard InChI:  InChI=1S/C28H32N2O6/c1-34-25-16-20(9-12-24(25)35-15-5-8-19-6-3-2-4-7-19)13-14-29-17-23(32)21-10-11-22(31)27-28(21)36-18-26(33)30-27/h2-4,6-7,9-12,16,23,29,31-32H,5,8,13-15,17-18H2,1H3,(H,30,33)/t23-/m1/s1

Standard InChI Key:  VAGMAHDJGBPZIB-HSZRJFAPSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.2964   -1.4973    0.0000 O   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 N   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
   -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 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
   -3.6486    1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -5.2475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -5.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073   -7.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2082   -8.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2134   -9.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151  -10.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8115   -9.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8063   -8.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5047   -7.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1154  -10.4797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4114   -9.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7153  -10.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0114   -9.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3153  -10.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6118   -9.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9134  -10.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9186  -11.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6222  -12.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3206  -11.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5172  -11.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792  -12.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -3.5999    0.0000 O   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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  2 10  2  0
  3  7  2  0
  5 11  2  0
 12 13  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 24 25  1  0
 25 26  1  0
 23 24  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 27 32  2  0
 26 27  1  0
 20 23  1  0
 33 34  1  0
 19 33  1  0
 14 15  1  0
 13 14  1  0
 12 35  1  1
 10 12  1  0
  7 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3797205

   ---

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: 492.57

Molecular Weight (Monoisotopic): 492.2260

AlogP: 3.61

#Rotatable Bonds: 12

Polar Surface Area: 109.28

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.56

CX Basic pKa: 9.57

CX LogP: 2.65

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.23

Np Likeness Score: -0.10

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