Methyl 3-(3-phenyl-1-(p-tolyl)-1H-pyrazole-4-carboxamido)propanoate

ID: ALA4756847

PubChem CID: 32171491

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)CCNC(=O)c1cn(-c2ccc(C)cc2)nc1-c1ccccc1

Standard InChI:  InChI=1S/C21H21N3O3/c1-15-8-10-17(11-9-15)24-14-18(21(26)22-13-12-19(25)27-2)20(23-24)16-6-4-3-5-7-16/h3-11,14H,12-13H2,1-2H3,(H,22,26)

Standard InChI Key:  INTTXTJVEZUDKM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.8699  -12.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7675  -11.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9620  -11.0728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5729  -11.7904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5865  -12.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6045  -13.2456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2850  -12.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6115  -10.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0771   -9.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7269   -8.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9115   -8.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4475   -9.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8002  -10.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9804  -13.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2074  -13.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0549  -14.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6745  -14.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4490  -14.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5979  -13.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0016  -12.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6981  -11.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5598   -8.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4137  -12.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1132  -11.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8288  -12.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4298  -13.1939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  9 10  2  0
 10 11  1  0
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  4  9  1  0
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 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 15  1  0
  8 21  1  0
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 12 23  1  0
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 24 25  1  0
 25 26  1  0
 24 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756847

   Methyl 3-[[1-(4-methylphenyl)-3-phenylpyrazole-4-carbonyl]amino]propanoate

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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 3.14

#Rotatable Bonds: 6

Polar Surface Area: 73.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.80

CX Basic pKa: 0.72

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -1.70

References

1. Zhao B,Liang Q,Ren H,Zhang X,Wu Y,Zhang K,Ma LY,Zheng YC,Liu HM.  (2020)  Discovery of pyrazole derivatives as cellular active inhibitors of histone lysine specific demethylase 5B (KDM5B/JARID1B).,  192  [PMID:32155529] [10.1016/j.ejmech.2020.112161]

2. Sayegh, Joyce J and 9 more authors.  2013-03-29  Identification of small molecule inhibitors of Jumonji AT-rich interactive domain 1B (JARID1B) histone demethylase by a sensitive high throughput screen.  [PMID:23408432]

3. Bavetsias, Vassilios and 42 more authors.  2016-02-25  8-Substituted Pyrido[3,4-d]pyrimidin-4(3H)-one Derivatives As Potent, Cell Permeable, KDM4 (JMJD2) and KDM5 (JARID1) Histone Lysine Demethylase Inhibitors.  [PMID:26741168]

4. Labadie, Sharada S SS and 19 more authors.  2016-09-15  Design and evaluation of 1,7-naphthyridones as novel KDM5 inhibitors.  [PMID:27499454]

5. Zheng, Yi-Chao YC and 5 more authors.  2019-01-01  Lysine demethylase 5B (KDM5B): A potential anti-cancer drug target.  [PMID:30343192]

6. Horton, John R and 22 more authors.  2018-12-13  Structure-Based Engineering of Irreversible Inhibitors against Histone Lysine Demethylase KDM5A.  [PMID:30392349]

7. Le Bihan, Yann-Vaï and 28 more authors.  2019-09-01  C8-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones: Studies towards the identification of potent, cell penetrant Jumonji C domain containing histone lysine demethylase 4 subfamily (KDM4) inhibitors, compound profiling in cell-based target engagement assays.  [PMID:31158747]

8. Zhao, Bing and 8 more authors.  2020-04-15  Discovery of pyrazole derivatives as cellular active inhibitors of histone lysine specific demethylase 5B (KDM5B/JARID1B).  [PMID:32155529]

Source

Source(1):

• Scientific Literature