(4-Chloro-1H-indol-2-yl)(4-(2-(4-methoxyphenoxy)ethyl)piperazin-1-yl)methanone

ID: ALA4474192

PubChem CID: 71724941

Max Phase: Preclinical

Molecular Formula: C22H24ClN3O3

Molecular Weight: 413.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(OCCN2CCN(C(=O)c3cc4c(Cl)cccc4[nH]3)CC2)cc1

Standard InChI:  InChI=1S/C22H24ClN3O3/c1-28-16-5-7-17(8-6-16)29-14-13-25-9-11-26(12-10-25)22(27)21-15-18-19(23)3-2-4-20(18)24-21/h2-8,15,24H,9-14H2,1H3

Standard InChI Key:  RNWJQFRWBPTMAA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.1693  -10.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8799  -10.0845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4563  -10.0888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949  -10.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3035  -10.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052   -9.2660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -8.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -9.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0133   -8.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7248   -9.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4369   -8.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1484   -9.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1437  -10.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8544  -10.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5676  -10.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5656   -9.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8543   -8.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2796  -10.5014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2801  -11.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5096  -11.8013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8401  -11.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859  -12.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7684  -12.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641  -13.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719  -13.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925  -13.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9973  -13.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145  -13.2783    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  3  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
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 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
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 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
  1 21  1  0
 21 24  1  0
 23 22  1  0
 22  1  2  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474192

   (4-chloro-1H-indol-2-yl)-[4-[2-(4-methoxyphenoxy)ethyl]piperazin-1-yl]methanone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 413.91

Molecular Weight (Monoisotopic): 413.1506

AlogP: 3.67

#Rotatable Bonds: 6

Polar Surface Area: 57.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 6.52

CX LogP: 3.23

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.38

References

1. Moritz AE, Free RB, Weiner WS, Akano EO, Gandhi D, Abramyan A, Keck TM, Ferrer M, Hu X, Southall N, Steiner J, Aubé J, Shi L, Frankowski KJ, Sibley DR..  (2020)  Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist.,  63  (10): [PMID:32342685] [10.1021/acs.jmedchem.0c00424]

Source

Source(1):

• Scientific Literature