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

ID: ALA4524376

PubChem CID: 155519993

Max Phase: Preclinical

Molecular Formula: C20H19ClN6O2S

Molecular Weight: 442.93

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccc(Cl)cc1)N1CCC(n2cc(-c3ncnc4[nH]ccc34)cn2)CC1

Standard InChI:  InChI=1S/C20H19ClN6O2S/c21-15-1-3-17(4-2-15)30(28,29)26-9-6-16(7-10-26)27-12-14(11-25-27)19-18-5-8-22-20(18)24-13-23-19/h1-5,8,11-13,16H,6-7,9-10H2,(H,22,23,24)

Standard InChI Key:  PKKMFPKIWKFGHU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   43.6674  -17.8941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.2586  -17.1809    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   42.8453  -17.8914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.1188  -15.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1188  -16.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8316  -17.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5444  -16.7679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.5444  -15.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8316  -15.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9749  -16.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4001  -15.5323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3999  -14.7053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6134  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1274  -15.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6137  -15.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3015  -15.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8938  -14.4032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0686  -14.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6550  -15.1189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8963  -15.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0723  -15.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8238  -16.6252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4943  -17.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1570  -16.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6871  -17.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4029  -16.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4056  -15.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6866  -15.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9738  -15.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1214  -15.5370    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
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  7  2  1  0
  2 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 21  1  0
 20 16  1  0
 20 21  2  0
 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:

   

   ALA4524376

   ---

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: 442.93

Molecular Weight (Monoisotopic): 442.0979

AlogP: 3.50

#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: 2.44

CX LogD: 2.44

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -1.66

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