1-(4-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-(pyrrolidin-1-yl)ethan-1-one

ID: ALA4554788

PubChem CID: 155556483

Max Phase: Preclinical

Molecular Formula: C20H25N7O

Molecular Weight: 379.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CN1CCCC1)N1CCC(n2cc(-c3ncnc4[nH]ccc34)cn2)CC1

Standard InChI:  InChI=1S/C20H25N7O/c28-18(13-25-7-1-2-8-25)26-9-4-16(5-10-26)27-12-15(11-24-27)19-17-3-6-21-20(17)23-14-22-19/h3,6,11-12,14,16H,1-2,4-5,7-10,13H2,(H,21,22,23)

Standard InChI Key:  UXJWYOCNOXYGNE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   26.1501   -3.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1501   -4.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8554   -4.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5607   -4.4244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5607   -3.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8554   -3.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4390   -3.2018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4388   -2.3835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6605   -2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1796   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6608   -3.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3624   -2.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9590   -2.0846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1425   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7333   -2.7928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -3.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1462   -3.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9003   -4.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5637   -4.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2195   -4.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2678   -4.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2666   -5.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9761   -4.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9737   -6.0608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0601   -6.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8592   -7.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2689   -6.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7229   -5.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 17  1  0
 16 12  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
  4 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554788

   ---

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: 379.47

Molecular Weight (Monoisotopic): 379.2121

AlogP: 2.08

#Rotatable Bonds: 4

Polar Surface Area: 82.94

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: 8.07

CX LogP: 0.53

CX LogD: -0.23

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -1.52

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