3-((3S,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile

ID: ALA459977

Cas Number: 1092578-48-7

PubChem CID: 9966538

Product Number: T127249, Order Now?

Max Phase: Preclinical

Molecular Formula: C16H20N6O

Molecular Weight: 312.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CCN(C(=O)CC#N)C[C@H]1N(C)c1ncnc2[nH]ccc12

Standard InChI:  InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13-/m1/s1

Standard InChI Key:  UJLAWZDWDVHWOW-DGCLKSJQSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -1.8252   -4.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -5.0713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131   -5.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -5.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -4.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131   -3.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5391   -5.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542   -5.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5379   -6.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9682   -5.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6879   -5.8922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3147   -3.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -5.4849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3117   -6.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0281   -5.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044   -6.7197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4059   -7.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -7.9584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240   -6.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -7.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8085   -7.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -7.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -6.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5 12  1  1
  5  6  1  0
  4 13  1  6
 13 14  1  0
  2  7  1  0
 13 15  1  0
  1  2  1  0
 14 16  2  0
  7  8  1  0
 16 17  1  0
  1  6  1  0
 17 18  2  0
 18 20  1  0
 19 14  1  0
 19 20  2  0
  7  9  2  0
  2  3  1  0
  8 10  1  0
  3  4  1  0
 10 11  3  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA459977

   (3S,4R)-Tofacitinib

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 312.38

Molecular Weight (Monoisotopic): 312.1699

AlogP: 1.54

#Rotatable Bonds: 3

Polar Surface Area: 88.91

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: 6.44

CX LogP: 1.24

CX LogD: 1.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.93

Np Likeness Score: -1.14

References

1. Jiang JK, Ghoreschi K, Deflorian F, Chen Z, Perreira M, Pesu M, Smith J, Nguyen DT, Liu EH, Leister W, Costanzi S, O'Shea JJ, Thomas CJ..  (2008)  Examining the chirality, conformation and selective kinase inhibition of 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile (CP-690,550).,  51  (24): [PMID:19053756] [10.1021/jm801142b]

Source

Source(1):

• Scientific Literature