5-(2-((2-(5-Bromo-2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)-amino)propyl)-1-(3-hydroxypropyl)indoline-7-carboxamide

ID: ALA3808726

PubChem CID: 123667086

Max Phase: Preclinical

Molecular Formula: C25H31BrF3N3O4

Molecular Weight: 574.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cc1cc2c(c(C(N)=O)c1)N(CCCO)CC2)NCCOc1cc(Br)ccc1OCC(F)(F)F

Standard InChI:  InChI=1S/C25H31BrF3N3O4/c1-16(31-6-10-35-22-14-19(26)3-4-21(22)36-15-25(27,28)29)11-17-12-18-5-8-32(7-2-9-33)23(18)20(13-17)24(30)34/h3-4,12-14,16,31,33H,2,5-11,15H2,1H3,(H2,30,34)

Standard InChI Key:  RWDAFKHZHMRDPE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300    3.7369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905    3.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380    5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2413    5.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2494    7.4828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -4.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337   -3.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446   -3.6095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   10.4890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2822   11.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891   12.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9990   13.9516    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9448   12.1605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549   13.3603    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1859    7.6025    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
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  9  5  1  0
  1 10  1  0
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 11 12  1  0
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 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  3 27  1  0
 27 28  2  0
 27 29  1  0
 22 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 19 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3808726

   ---

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: 574.44

Molecular Weight (Monoisotopic): 573.1450

AlogP: 3.83

#Rotatable Bonds: 13

Polar Surface Area: 97.05

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.65

CX LogP: 3.82

CX LogD: 1.61

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.32

Np Likeness Score: -0.86

References

1. Zhao F, Li J, Chen Y, Tian Y, Wu C, Xie Y, Zhou Y, Wang J, Xie X, Liu H..  (2016)  Design, Synthesis, and Biological Evaluation of Indoline and Indole Derivatives as Potent and Selective α1A-Adrenoceptor Antagonists.,  59  (8): [PMID:27031406] [10.1021/acs.jmedchem.5b02023]

Source

Source(1):

• Scientific Literature