Ethyl 5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)-4-oxo-2-(o-tolylamino)-4,5-dihydrofuran-3-carboxylate

ID: ALA4098908

PubChem CID: 137662296

Max Phase: Preclinical

Molecular Formula: C21H17N3O4

Molecular Weight: 375.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(Nc2ccccc2C)O/C(=C\c2c[nH]c3ncccc23)C1=O

Standard InChI:  InChI=1S/C21H17N3O4/c1-12-6-3-4-8-15(12)24-20-17(21(26)27-2)18(25)16(28-20)10-13-11-23-19-14(13)7-5-9-22-19/h3-11,24H,1-2H3,(H,22,23)/b16-10-

Standard InChI Key:  XFVMQJXQUHWCFH-YBEGLDIGSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   17.8378  -10.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6550  -10.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9094   -9.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2464   -9.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5877   -9.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2452   -8.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1346  -11.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9474  -11.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4229  -11.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2350  -11.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5690  -10.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0848  -10.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2744  -10.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6870   -9.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2935  -10.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8580   -8.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6355   -8.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8104   -9.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2034  -10.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5434  -11.1766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2897  -10.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9962  -10.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4029   -9.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9959   -9.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1824   -9.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7776   -9.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1869  -10.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0880  -12.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  2  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  5 18  2  0
 18 19  1  0
 19 23  1  0
 22 20  1  0
 20 21  1  0
 21 19  2  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
  9 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098908

   ---

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: 375.38

Molecular Weight (Monoisotopic): 375.1219

AlogP: 3.31

#Rotatable Bonds: 4

Polar Surface Area: 93.31

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.80

CX Basic pKa: 3.25

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -0.80

References

1. Irie T, Asami T, Sawa A, Uno Y, Hanada M, Taniyama C, Funakoshi Y, Masai H, Sawa M..  (2017)  Discovery of novel furanone derivatives as potent Cdc7 kinase inhibitors.,  130  [PMID:28279847] [10.1016/j.ejmech.2017.02.030]

Source

Source(1):

• Scientific Literature