3-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-10H-phenothiazine

ID: ALA3808576

PubChem CID: 127044215

Max Phase: Preclinical

Molecular Formula: C23H22N4S

Molecular Weight: 386.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc2c(C)cc(C)nc2n1Cc1ccc2c(c1)Sc1ccccc1N2

Standard InChI:  InChI=1S/C23H22N4S/c1-4-21-26-22-14(2)11-15(3)24-23(22)27(21)13-16-9-10-18-20(12-16)28-19-8-6-5-7-17(19)25-18/h5-12,25H,4,13H2,1-3H3

Standard InChI Key:  NKAANKFUNNICAL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5002    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1981   -1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -0.7456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0841    1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6174    0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8402   -0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8436   -1.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2980   -2.7961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7869   -3.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7835   -1.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3155   -0.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1128    0.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1641   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4847    1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105    2.8719    0.0000 C   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
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  5  8  1  0
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 14  9  1  0
 12 15  1  0
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 19 17  1  0
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 22 23  1  0
 23 24  2  0
 24 19  1  0
 24 25  1  0
 22 26  1  0
 18 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3808576

   ---

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: 386.52

Molecular Weight (Monoisotopic): 386.1565

AlogP: 5.87

#Rotatable Bonds: 3

Polar Surface Area: 42.74

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.45

CX LogP: 5.48

CX LogD: 5.48

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.53

References

1. Fukuda H, Ito S, Watari K, Mogi C, Arisawa M, Okajima F, Kurose H, Shuto S..  (2016)  Identification of a Potent and Selective GPR4 Antagonist as a Drug Lead for the Treatment of Myocardial Infarction.,  7  (5): [PMID:27190599] [10.1021/acsmedchemlett.6b00014]

Source

Source(1):

• Scientific Literature