4-(1-(1-Tosylpiperidin-4-yl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA4525281

PubChem CID: 155538799

Max Phase: Preclinical

Molecular Formula: C21H22N6O2S

Molecular Weight: 422.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)N2CCC(n3cc(-c4ncnc5[nH]ccc45)cn3)CC2)cc1

Standard InChI:  InChI=1S/C21H22N6O2S/c1-15-2-4-18(5-3-15)30(28,29)26-10-7-17(8-11-26)27-13-16(12-25-27)20-19-6-9-22-21(19)24-14-23-20/h2-6,9,12-14,17H,7-8,10-11H2,1H3,(H,22,23,24)

Standard InChI Key:  ZCUACLFMEQKGCE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   19.8524  -11.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4438  -10.4723    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0306  -11.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3051   -9.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3051  -10.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0175  -10.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7299  -10.0596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7299   -9.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0175   -8.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1596  -10.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5868   -8.8246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5866   -7.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8005   -7.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3147   -8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8008   -9.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4892   -8.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0818   -7.6961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2570   -7.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8437   -8.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0843   -9.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2608   -9.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0124   -9.9170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6825  -10.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3449   -9.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8715  -10.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5869  -10.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5896   -9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8710   -8.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1586   -9.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3051   -8.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 17 18  1  0
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 19 21  1  0
 20 16  1  0
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 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
 10 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 10  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525281

   ---

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: 422.51

Molecular Weight (Monoisotopic): 422.1525

AlogP: 3.16

#Rotatable Bonds: 4

Polar Surface Area: 96.77

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 3.91

CX LogP: 2.35

CX LogD: 2.35

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -1.57

References

1. Jiang F, Zang L, Miao X, Jia F, Wang J, Zhu M, Gong P, Jiang N, Zhai X..  (2019)  Design, synthesis and anti-inflammatory evaluation of novel pyrrolo[2,3-d]pyrimidin derivatives as potent JAK inhibitors.,  27  (18): [PMID:31378597] [10.1016/j.bmc.2019.07.037]

Source

Source(1):

• Scientific Literature