(Z)-(tetrahydrofuran-2-yl)methyl 3-((6-chloropyridin-3-yl)methylamino)-2-cyano-3-(methylthio)acrylate

ID: ALA2273018

PubChem CID: 76327060

Max Phase: Preclinical

Molecular Formula: C16H18ClN3O3S

Molecular Weight: 367.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS/C(NCc1ccc(Cl)nc1)=C(/C#N)C(=O)OCC1CCCO1

Standard InChI:  InChI=1S/C16H18ClN3O3S/c1-24-15(20-9-11-4-5-14(17)19-8-11)13(7-18)16(21)23-10-12-3-2-6-22-12/h4-5,8,12,20H,2-3,6,9-10H2,1H3/b15-13-

Standard InChI Key:  AGVSEXVXEIXTCE-SQFISAMPSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   17.5778   -2.0362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3932   -2.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8001   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3928   -0.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5742   -0.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1710   -1.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3538   -1.3370    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.6173   -1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0258   -2.0408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8429   -2.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2514   -2.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0686   -2.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8426   -3.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4357   -4.1650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4770   -3.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4773   -2.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2517   -1.3334    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.0689   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2942   -3.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7026   -4.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3682   -4.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9753   -5.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6832   -5.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5134   -4.2447    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
 23 24  1  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2273018

   oxolan-2-ylmethyl (Z)-3-[(6-chloropyridin-3-yl)methylamino]-2-cyano-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: 367.86

Molecular Weight (Monoisotopic): 367.0757

AlogP: 2.64

#Rotatable Bonds: 7

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: ┄

CX LogP: 2.86

CX LogD: 2.86

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.34

Np Likeness Score: -1.06

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