N-(2-molpholinoethyl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazole-4-carboxamide

ID: ALA4755899

PubChem CID: 162655328

Max Phase: Preclinical

Molecular Formula: C21H23N5O2

Molecular Weight: 377.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCCN1CCOCC1)c1cn(-c2ccccc2)nc1-c1ccncc1

Standard InChI:  InChI=1S/C21H23N5O2/c27-21(23-10-11-25-12-14-28-15-13-25)19-16-26(18-4-2-1-3-5-18)24-20(19)17-6-8-22-9-7-17/h1-9,16H,10-15H2,(H,23,27)

Standard InChI Key:  TTWOHLHTNDZLHZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.8290   -4.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7257   -4.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9124   -3.9579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5196   -4.6824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5525   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5707   -6.1515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2577   -4.8985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9811   -5.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6863   -4.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4097   -5.2636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4240   -6.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1432   -6.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8509   -6.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8347   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1107   -4.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5586   -3.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0286   -2.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6751   -1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8519   -1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3834   -2.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7395   -3.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9310   -6.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1506   -6.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9966   -7.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6221   -7.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4041   -7.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5544   -6.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
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  5  1  2  0
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  9 10  1  0
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 14 15  1  0
 15 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
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  4 17  1  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
  1 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755899

   ---

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: 377.45

Molecular Weight (Monoisotopic): 377.1852

AlogP: 2.00

#Rotatable Bonds: 6

Polar Surface Area: 72.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.79

CX Basic pKa: 6.07

CX LogP: 1.75

CX LogD: 1.73

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -2.22

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