(1,3-diphenyl-1H-pyrazol-4-yl)(4-(2-(pyrrolidin-1-yl)ethyl)piperazin-1-yl)methanone

ID: ALA4776171

PubChem CID: 8107007

Max Phase: Preclinical

Molecular Formula: C26H31N5O

Molecular Weight: 429.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1cn(-c2ccccc2)nc1-c1ccccc1)N1CCN(CCN2CCCC2)CC1

Standard InChI:  InChI=1S/C26H31N5O/c32-26(30-19-17-29(18-20-30)16-15-28-13-7-8-14-28)24-21-31(23-11-5-2-6-12-23)27-25(24)22-9-3-1-4-10-22/h1-6,9-12,21H,7-8,13-20H2

Standard InChI Key:  LJEWEWGANFCCLU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    4.1924   -5.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310   -5.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8286   -4.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -4.1060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -4.8237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6476   -5.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6657   -6.2789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3461   -5.0377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6727   -3.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1382   -2.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881   -1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -1.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086   -2.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613   -3.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415   -6.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686   -6.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -7.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356   -7.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5102   -7.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -6.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0627   -5.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7592   -5.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7454   -4.1981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0289   -3.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3263   -4.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4455   -3.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1606   -4.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8607   -3.7507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6120   -4.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1476   -3.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7261   -2.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9300   -2.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  4  9  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 15  1  0
  8 21  1  0
  8 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776171

   (1,3-Diphenylpyrazol-4-yl)-[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]methanone

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: 429.57

Molecular Weight (Monoisotopic): 429.2529

AlogP: 3.39

#Rotatable Bonds: 6

Polar Surface Area: 44.61

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.15

CX LogP: 3.66

CX LogD: 1.91

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -1.72

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