(S)-3-{3-[1-(2-Fluoro-pyridin-4-yl)-pyrrolidin-3-yloxy]-phenylamino}-4-(1H-indol-3-yl)-pyrrole-2,5-dione

ID: ALA3114761

PubChem CID: 76310565

Max Phase: Preclinical

Molecular Formula: C27H22FN5O3

Molecular Weight: 483.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(c2c[nH]c3ccccc23)=C1Nc1cccc(O[C@H]2CCN(c3ccnc(F)c3)C2)c1

Standard InChI:  InChI=1S/C27H22FN5O3/c28-23-13-17(8-10-29-23)33-11-9-19(15-33)36-18-5-3-4-16(12-18)31-25-24(26(34)32-27(25)35)21-14-30-22-7-2-1-6-20(21)22/h1-8,10,12-14,19,30H,9,11,15H2,(H2,31,32,34,35)/t19-/m0/s1

Standard InChI Key:  ULLVSXLCIMTNQM-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
   18.5818  -20.7688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8509  -19.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6630  -19.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9344  -19.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3948  -18.4324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5803  -18.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3127  -19.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7451  -18.9036    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.7948  -21.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7795  -21.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5580  -22.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0544  -21.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0673  -22.2506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2545  -23.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2633  -24.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9832  -24.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9615  -22.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6822  -23.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6924  -24.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4861  -24.3082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9665  -23.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4696  -22.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7105  -22.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4922  -21.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4820  -21.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6939  -20.8408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2172  -21.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3919  -21.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1437  -20.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2124  -22.3069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9182  -21.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6388  -22.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3442  -21.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3270  -21.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5986  -20.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8963  -21.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  2  1  0
  4  8  1  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  1  1  0
 10 13  1  6
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 22 23  1  0
 27 28  2  0
 25 29  2  0
 24 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 33 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114761

   3-[3-[(3S)-1-(2-fluoropyridin-4-yl)pyrrolidin-3-yl]oxyanilino]-4-(1H-indol-3-yl)pyrrole-2,5-dione

Molecule Features

Natural Product: No

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: 483.50

Molecular Weight (Monoisotopic): 483.1707

AlogP: 3.84

#Rotatable Bonds: 6

Polar Surface Area: 99.35

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.57

CX Basic pKa: 2.72

CX LogP: 3.07

CX LogD: 3.06

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: -0.72

References

1. McDonnell ME, Bian H, Wrobel J, Smith GR, Liang S, Ma H, Reitz AB..  (2014)  Anilino-monoindolylmaleimides as potent and selective JAK3 inhibitors.,  24  (4): [PMID:24461299] [10.1016/j.bmcl.2014.01.001]

Source

Source(1):

• Scientific Literature