(E)-4-(1-methyl-1H-pyrazol-4-yl)-3-(3-(4-(morpholinomethyl)phenylamino)-3-oxoprop-1-enyl)pyridine 1-oxide

ID: ALA4070538

PubChem CID: 137638333

Max Phase: Preclinical

Molecular Formula: C23H25N5O3

Molecular Weight: 419.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cc[n+]([O-])cc2/C=C/C(=O)Nc2ccc(CN3CCOCC3)cc2)cn1

Standard InChI:  InChI=1S/C23H25N5O3/c1-26-16-20(14-24-26)22-8-9-28(30)17-19(22)4-7-23(29)25-21-5-2-18(3-6-21)15-27-10-12-31-13-11-27/h2-9,14,16-17H,10-13,15H2,1H3,(H,25,29)/b7-4+

Standard InChI Key:  JKZKMTHMOLQVNI-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   16.4167   -6.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4156   -7.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1236   -7.4234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8333   -7.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8304   -6.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1218   -5.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5366   -5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2458   -6.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9520   -5.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6612   -6.1807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9489   -4.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3674   -5.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0727   -6.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7783   -5.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7757   -4.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0615   -4.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3587   -4.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4813   -4.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1911   -4.9412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1918   -5.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8975   -6.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6055   -5.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6033   -4.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8931   -4.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1194   -4.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7769   -4.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5220   -3.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7048   -3.7090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4547   -4.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2224   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1234   -8.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  6 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 25  2  0
 28 30  1  0
  3 31  1  0
M  CHG  2   3   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4070538

   ---

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: 419.49

Molecular Weight (Monoisotopic): 419.1957

AlogP: 2.20

#Rotatable Bonds: 6

Polar Surface Area: 86.33

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.77

CX LogP: 0.89

CX LogD: 0.80

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.70

References

1. Fujimoto J, Hirayama T, Hirata Y, Hikichi Y, Murai S, Hasegawa M, Hasegawa Y, Yonemori K, Hata A, Aoyama K, Cary DR..  (2017)  Studies of CDK 8/19 inhibitors: Discovery of novel and selective CDK8/19 dual inhibitors and elimination of their CYP3A4 time-dependent inhibition potential.,  25  (12): [PMID:28392276] [10.1016/j.bmc.2017.03.049]

Source

Source(1):

• Scientific Literature