(Z)-2-ethoxyethyl 2-cyano-3-(methylthio)-3-((6-propoxypyridin-3-yl)methylamino)acrylate

ID: ALA2273013

PubChem CID: 76308930

Max Phase: Preclinical

Molecular Formula: C18H25N3O4S

Molecular Weight: 379.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(CN/C(SC)=C(\C#N)C(=O)OCCOCC)cn1

Standard InChI:  InChI=1S/C18H25N3O4S/c1-4-8-24-16-7-6-14(12-20-16)13-21-17(26-3)15(11-19)18(22)25-10-9-23-5-2/h6-7,12,21H,4-5,8-10,13H2,1-3H3/b17-15-

Standard InChI Key:  POOZOUOMGARTGS-ICFOKQHNSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   30.1205   -7.5832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9359   -7.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3428   -6.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9354   -6.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1169   -6.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7136   -6.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8965   -6.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1600   -6.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5684   -7.5878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3856   -7.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7940   -8.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6112   -8.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3852   -9.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9784   -9.7120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0196   -9.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0200   -7.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7944   -6.8804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.6115   -6.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8368   -9.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2452   -9.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0624   -9.7120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4712   -9.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2884   -9.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4858   -6.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6686   -6.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2579   -5.4735    0.0000 C   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
  6  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  3  0
 12 15  1  0
 12 16  2  0
 10 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2273013

   2-ethoxyethyl (Z)-2-cyano-3-methylsulfanyl-3-[(6-propoxypyridin-3-yl)methylamino]prop-2-enoate

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: 379.48

Molecular Weight (Monoisotopic): 379.1566

AlogP: 2.64

#Rotatable Bonds: 12

Polar Surface Area: 93.47

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.59

CX LogP: 3.24

CX LogD: 3.24

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.26

Np Likeness Score: -1.53

References

1. Wang Q, Sun H, Cao H, Cheng M, Huang R..  (2003)  Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates.,  51  (17): [PMID:12903965] [10.1021/jf034067s]

Source

Source(1):

• Scientific Literature