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

ID: ALA2273020

PubChem CID: 76316125

Max Phase: Preclinical

Molecular Formula: C14H14ClN3O2S

Molecular Weight: 323.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCOC(=O)/C(C#N)=C(/NCc1ccc(Cl)nc1)SC

Standard InChI:  InChI=1S/C14H14ClN3O2S/c1-3-6-20-14(19)11(7-16)13(21-2)18-9-10-4-5-12(15)17-8-10/h3-5,8,18H,1,6,9H2,2H3/b13-11-

Standard InChI Key:  TWFMWKJDKGRUQQ-QBFSEMIESA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    1.6343   -1.8298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497   -1.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8567   -1.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493   -0.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6307   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275   -1.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -1.1307    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6738   -1.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -1.8345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8995   -1.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -2.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1251   -2.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -3.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922   -3.9587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5335   -3.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338   -1.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1254   -1.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3507   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7591   -3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5763   -3.9587    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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2273020

   prop-2-enyl (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: 323.81

Molecular Weight (Monoisotopic): 323.0495

AlogP: 2.65

#Rotatable Bonds: 7

Polar Surface Area: 75.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.27

Np Likeness Score: -1.26

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