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

ID: ALA4474807

PubChem CID: 155537166

Max Phase: Preclinical

Molecular Formula: C21H22N6O3S

Molecular Weight: 438.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCC(n3cc(-c4ncnc5[nH]ccc45)cn3)CC2)cc1

Standard InChI:  InChI=1S/C21H22N6O3S/c1-30-17-2-4-18(5-3-17)31(28,29)26-10-7-16(8-11-26)27-13-15(12-25-27)20-19-6-9-22-21(19)24-14-23-20/h2-6,9,12-14,16H,7-8,10-11H2,1H3,(H,22,23,24)

Standard InChI Key:  LJHHJSANPHUPQM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   42.7185  -11.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3097  -10.2938    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.8964  -11.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1700   -9.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1700   -9.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8827  -10.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5955   -9.8809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5955   -9.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8827   -8.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0259   -9.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4514   -8.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4512   -7.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6646   -7.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1786   -8.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6649   -8.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3528   -8.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9451   -7.5163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1201   -7.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7064   -8.2320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9476   -8.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1237   -8.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8752   -9.7383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5456  -10.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2084   -9.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7381  -10.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4538   -9.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4566   -9.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7376   -8.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0249   -9.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1724   -8.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.8871   -9.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 10  1  0
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 20 16  1  0
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 23 24  2  0
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 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
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474807

   ---

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: 438.51

Molecular Weight (Monoisotopic): 438.1474

AlogP: 2.86

#Rotatable Bonds: 5

Polar Surface Area: 106.00

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 3.91

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -1.44

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