(Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one

ID: ALA4102902

PubChem CID: 86681992

Max Phase: Preclinical

Molecular Formula: C21H20N4O3

Molecular Weight: 376.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2c[nH]c3ncccc23)Oc2c1ccc(O)c2CN1CCNCC1

Standard InChI:  InChI=1S/C21H20N4O3/c26-17-4-3-15-19(27)18(10-13-11-24-21-14(13)2-1-5-23-21)28-20(15)16(17)12-25-8-6-22-7-9-25/h1-5,10-11,22,26H,6-9,12H2,(H,23,24)/b18-10-

Standard InChI Key:  JKEWQEZHKJUJJG-ZDLGFXPLSA-N

Molfile:  

     RDKit          2D

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   24.3935   -5.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1015   -5.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0997   -3.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0973   -3.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3884   -2.6226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3840   -1.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6792   -1.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9703   -1.8028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9707   -2.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6801   -3.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8084   -4.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8132   -5.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5976   -5.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0776   -4.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5898   -3.9926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8546   -6.1002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8947   -4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2992   -3.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1082   -3.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2734   -3.0514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9593   -3.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5618   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3884   -1.8567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6131   -1.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0110   -2.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1875   -2.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6868   -3.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 13  2  0
 12  4  2  0
  4  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 14 17  2  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 23  1  0
 22 19  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102902

   (2Z)-6-hydroxy-7-(piperazin-1-ylmethyl)-2-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)-1-benzofuran-3-one

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: 376.42

Molecular Weight (Monoisotopic): 376.1535

AlogP: 2.29

#Rotatable Bonds: 3

Polar Surface Area: 90.48

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.86

CX Basic pKa: 9.12

CX LogP: 0.45

CX LogD: 0.39

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.69

References

1. Nakano H, Hasegawa T, Kojima H, Okabe T, Nagano T..  (2017)  Design and Synthesis of Potent and Selective PIM Kinase Inhibitors by Targeting Unique Structure of ATP-Binding Pocket.,  8  (5): [PMID:28523101] [10.1021/acsmedchemlett.6b00518]

Source

Source(1):

• Scientific Literature