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

ID: ALA3800341

PubChem CID: 127047859

Max Phase: Preclinical

Molecular Formula: C28H32N2O5

Molecular Weight: 476.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCNCCc2ccc(O)c3c2OCC(=O)N3)ccc1OCCCc1ccccc1

Standard InChI:  InChI=1S/C28H32N2O5/c1-33-25-18-21(9-12-24(25)34-17-5-8-20-6-3-2-4-7-20)13-15-29-16-14-22-10-11-23(31)27-28(22)35-19-26(32)30-27/h2-4,6-7,9-12,18,29,31H,5,8,13-17,19H2,1H3,(H,30,32)

Standard InChI Key:  XFQRGEPJIICUBL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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   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
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   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
    1.2964    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  1  6  1  0
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  8  9  2  0
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 25 26  1  0
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 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
 10 12  1  0
  7 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800341

   ---

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: 476.57

Molecular Weight (Monoisotopic): 476.2311

AlogP: 4.12

#Rotatable Bonds: 12

Polar Surface Area: 89.05

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.97

CX Basic pKa: 10.18

CX LogP: 3.40

CX LogD: 2.11

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: -0.09

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