(Z)-2-methoxyethyl 2-cyano-3-((6-methoxypyridin-3-yl)methylamino)-3-(methylthio)acrylate

ID: ALA2273011

PubChem CID: 76316124

Max Phase: Preclinical

Molecular Formula: C15H19N3O4S

Molecular Weight: 337.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOC(=O)/C(C#N)=C(/NCc1ccc(OC)nc1)SC

Standard InChI:  InChI=1S/C15H19N3O4S/c1-20-6-7-22-15(19)12(8-16)14(23-3)18-10-11-4-5-13(21-2)17-9-11/h4-5,9,18H,6-7,10H2,1-3H3/b14-12-

Standard InChI Key:  PVUSWBMFJAXOON-OWBHPGMISA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    8.5557  -11.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3711  -11.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7780  -10.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3706   -9.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5521   -9.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1489  -10.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3317  -10.6893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5952  -10.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0036  -11.3931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8208  -11.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2292  -12.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0464  -12.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8205  -12.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4136  -13.5173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4549  -12.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4552  -11.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2296  -10.6857    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0468  -10.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2720  -12.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6805  -13.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4977  -13.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9064  -12.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -9.9828    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
  7 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2273011

   2-methoxyethyl (Z)-2-cyano-3-[(6-methoxypyridin-3-yl)methylamino]-3-methylsulfanylprop-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: 337.40

Molecular Weight (Monoisotopic): 337.1096

AlogP: 1.47

#Rotatable Bonds: 9

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: 1.63

CX LogP: 2.00

CX LogD: 2.00

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.31

Np Likeness Score: -1.50

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