N-(2-amino-4-fluoro-phenyl)-3-(1-cinnamylpyrazol-4-yl)prop-2-enamide

ID: ALA5195471

PubChem CID: 68294530

Max Phase: Preclinical

Molecular Formula: C21H19FN4O

Molecular Weight: 362.41

Names and Identifiers

Canonical SMILES:  Nc1cc(F)ccc1NC(=O)C=Cc1cnn(CC=Cc2ccccc2)c1

Standard InChI:  InChI=1S/C21H19FN4O/c22-18-9-10-20(19(23)13-18)25-21(27)11-8-17-14-24-26(15-17)12-4-7-16-5-2-1-3-6-16/h1-11,13-15H,12,23H2,(H,25,27)

Standard InChI Key:  BLVQHYHDYFTPDV-UHFFFAOYSA-N

Molfile:  

 
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   -4.9659    0.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2540    0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2540   -0.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8247    0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1101    0.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3954    0.0430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420    0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5025   -0.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092   -0.7772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7345   -0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    0.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    0.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839    1.1939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.2344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2085   -0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    0.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4433    0.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558   -0.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -0.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    1.1938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6804   -0.2355    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
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  7  8  2  3
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 15 16  2  3
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 22 21  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5195471

   (E)-N-(2-amino-4-fluorophenyl)-3-[1-[(E)-3-phenylprop-2-enyl]pyrazol-4-yl]prop-2-enamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 362.41

Molecular Weight (Monoisotopic): 362.1543

AlogP: 3.97

#Rotatable Bonds: 6

Polar Surface Area: 72.94

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.46

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.36

References

1. Moreno-Yruela C, Olsen CA..  (2022)  Determination of Slow-Binding HDAC Inhibitor Potency and Subclass Selectivity.,  13  (5.0): [PMID:35586419] [10.1021/acsmedchemlett.1c00702]

Source

Source(1):

• Scientific Literature