(Z)-2-methoxyethyl 2-cyano-3-(methylthio)-3-(pyridin-3-ylmethylamino)acrylate

ID: ALA2273012

PubChem CID: 76327058

Max Phase: Preclinical

Molecular Formula: C14H17N3O3S

Molecular Weight: 307.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOC(=O)/C(C#N)=C(/NCc1cccnc1)SC

Standard InChI:  InChI=1S/C14H17N3O3S/c1-19-6-7-20-14(18)12(8-15)13(21-2)17-10-11-4-3-5-16-9-11/h3-5,9,17H,6-7,10H2,1-2H3/b13-12-

Standard InChI Key:  CRGZXHKCCJUBTE-SEYXRHQNSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    0.7759  -11.5824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913  -11.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9982  -10.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908  -10.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723  -10.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691  -10.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154  -10.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238  -11.5871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0410  -11.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494  -12.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666  -12.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0406  -13.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6338  -13.7113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750  -13.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6754  -11.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498  -10.8797    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2670  -10.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4922  -13.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9006  -13.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7178  -13.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1266  -13.0037    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
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  3  0
 11 14  1  0
 11 15  2  0
  9 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2273012

   2-methoxyethyl (Z)-2-cyano-3-methylsulfanyl-3-(pyridin-3-ylmethylamino)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: 307.38

Molecular Weight (Monoisotopic): 307.0991

AlogP: 1.46

#Rotatable Bonds: 8

Polar Surface Area: 84.24

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.82

CX LogP: 1.57

CX LogD: 1.57

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.34

Np Likeness Score: -1.38

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