5-(2-((2-(5-Fluoro-2-methoxyphenoxy)ethyl)amino)propyl)-1-(3-hydroxypropyl)-1H-indole-7-carboxamide

ID: ALA3810110

PubChem CID: 123562321

Max Phase: Preclinical

Molecular Formula: C24H30FN3O4

Molecular Weight: 443.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(F)cc1OCCNC(C)Cc1cc(C(N)=O)c2c(ccn2CCCO)c1

Standard InChI:  InChI=1S/C24H30FN3O4/c1-16(27-7-11-32-22-15-19(25)4-5-21(22)31-2)12-17-13-18-6-9-28(8-3-10-29)23(18)20(14-17)24(26)30/h4-6,9,13-16,27,29H,3,7-8,10-12H2,1-2H3,(H2,26,30)

Standard InChI Key:  ZPZSLCYMUPFPPB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -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
   -7.5527    8.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8467    7.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.1609    9.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5629    9.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -6.2797   11.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1859    7.6025    0.0000 F   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
  8  9  2  0
  9  5  1  0
  1 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 12 14  1  0
 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
 19 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3810110

   ---

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: 443.52

Molecular Weight (Monoisotopic): 443.2220

AlogP: 2.87

#Rotatable Bonds: 12

Polar Surface Area: 98.74

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.52

CX LogP: 2.41

CX LogD: 0.31

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -0.83

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