(E)-1-(benzo[d]thiazol-2-yl)-4-((3-hydroxypropylamino)methylene)-3-phenyl-1H-pyrazol-5(4H)-one

ID: ALA4093427

Max Phase: Preclinical

Molecular Formula: C20H18N4O2S

Molecular Weight: 378.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/NCCCO)C(c2ccccc2)=NN1c1nc2ccccc2s1

Standard InChI:  InChI=1S/C20H18N4O2S/c25-12-6-11-21-13-15-18(14-7-2-1-3-8-14)23-24(19(15)26)20-22-16-9-4-5-10-17(16)27-20/h1-5,7-10,13,21,25H,6,11-12H2/b15-13+

Standard InChI Key:  RQYROBYFFYZJNY-FYWRMAATSA-N

Molfile:  

     RDKit          2D

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    7.6569  -14.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0342  -15.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8527  -15.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2924  -14.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0982  -14.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9105  -14.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1899  -13.3305    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504  -12.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8758  -13.2822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5755  -12.0129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2538  -11.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0300  -10.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2132  -10.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9325  -11.5086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7989  -10.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2004   -9.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7837   -8.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9657   -8.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5661   -9.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9851  -10.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0212  -11.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5343  -10.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2298   -9.3697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6017   -8.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4178   -8.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7898   -7.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6059   -7.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
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  8 10  1  0
 15 16  2  0
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 20 15  1  0
 13 15  1  0
 11 21  2  0
 12 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093427

   ---

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: 378.46

Molecular Weight (Monoisotopic): 378.1150

AlogP: 2.90

#Rotatable Bonds: 6

Polar Surface Area: 77.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.94

CX LogP: 2.80

CX LogD: 2.80

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.42

References

1. Frimurer TM, Mende F, Graae AS, Engelstoft MS, Egerod KL, Nygaard R, Gerlach LO, Hansen JB, Schwartz TW, Holst B..  (2017)  Model-Based Discovery of Synthetic Agonists for the Zn2+-Sensing G-Protein-Coupled Receptor 39 (GPR39) Reveals Novel Biological Functions.,  60  (3): [PMID:28045522] [10.1021/acs.jmedchem.6b00648]

Source

Source(1):

• Scientific Literature