(+/-)-cis-3-[3-(Dipyrrolo[2,3-b:20,30-d]pyridin-1(6H)-yl)-4-methylpiperidin-1-yl]-3-oxopropanenitrile

ID: ALA5281283

Max Phase: Preclinical

Molecular Formula: C18H19N5O

Molecular Weight: 321.38

Names and Identifiers

Canonical SMILES:  C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1n1ccc2cnc3[nH]ccc3c21

Standard InChI:  InChI=1S/C18H19N5O/c1-12-4-8-22(16(24)2-6-19)11-15(12)23-9-5-13-10-21-18-14(17(13)23)3-7-20-18/h3,5,7,9-10,12,15H,2,4,8,11H2,1H3,(H,20,21)/t12-,15+/m1/s1

Standard InChI Key:  UQVAOELSLJXOMB-DOMZBBRYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -0.2774    1.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120    2.0205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9909    1.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989    2.1844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043    1.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043    0.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    0.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9909    0.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909    0.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782   -0.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907   -0.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    0.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -0.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5116   -1.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335   -2.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0678   -1.1830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102   -0.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -0.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357   -1.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -1.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0153   -1.1263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691   -0.1816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014   -1.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  7  6  1  0
  8  7  2  0
  3  8  1  0
  8  9  1  0
  9  1  2  0
  7 10  1  0
 10 11  1  0
 12 11  2  0
  6 12  1  0
 13 10  1  6
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 13 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  3  0
 19 23  2  0
 14 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5281283

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.38

Molecular Weight (Monoisotopic): 321.1590

AlogP: 2.84

#Rotatable Bonds: 2

Polar Surface Area: 77.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: 5.21

CX LogP: 1.57

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -0.83

References

1. Yamagishi H, Inoue T, Nakajima Y, Maeda J, Tominaga H, Usuda H, Hondo T, Moritomo A, Nakamori F, Ito M, Nakamura K, Morio H, Higashi Y, Inami M, Shirakami S..  (2017)  Discovery of tricyclic dipyrrolopyridine derivatives as novel JAK inhibitors.,  25  (20.0): [PMID:28789911] [10.1016/j.bmc.2017.07.043]

2. Yamagishi H, Inoue T, Nakajima Y, Maeda J, Tominaga H, Usuda H, Hondo T, Moritomo A, Nakamori F, Ito M, Nakamura K, Morio H, Higashi Y, Inami M, Shirakami S..  (2017)  Discovery of tricyclic dipyrrolopyridine derivatives as novel JAK inhibitors.,  25  (20.0): [PMID:28789911] [10.1016/j.bmc.2017.07.043]

Source

Source(1):

• Scientific Literature