2-ethoxyethyl 2-cyano-3-((3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)methylamino)-3-(methylthio)acrylate

ID: ALA2229424

PubChem CID: 42604421

Max Phase: Preclinical

Molecular Formula: C18H19FN4O4S

Molecular Weight: 406.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOCCOC(=O)/C(C#N)=C(\NCc1nc(-c2ccc(F)cc2)no1)SC

Standard InChI:  InChI=1S/C18H19FN4O4S/c1-3-25-8-9-26-18(24)14(10-20)17(28-2)21-11-15-22-16(23-27-15)12-4-6-13(19)7-5-12/h4-7,21H,3,8-9,11H2,1-2H3/b17-14+

Standard InChI Key:  LRWATZSWWNAMQM-SAPNQHFASA-N

Molfile:  

     RDKit          2D

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   17.0124  -16.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4210  -17.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4210  -16.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2382  -16.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0124  -15.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6468  -16.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4640  -16.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8726  -16.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6898  -16.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0984  -16.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8315  -18.3773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7866  -16.2552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9693  -16.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6063  -15.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9866  -14.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4151  -14.2108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6829  -14.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8020  -15.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9557  -14.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9231  -13.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1999  -12.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5087  -13.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5454  -14.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2690  -14.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7842  -13.0596    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7866  -17.6706    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9695  -17.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  4  5  1  0
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  9 10  1  0
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  3 12  3  0
  1 13  1  0
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 15 16  1  0
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 20 21  2  0
 21 22  1  0
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 25 20  1  0
 18 20  1  0
 23 26  1  0
  1 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229424

   2-ethoxyethyl (E)-2-cyano-3-[[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-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: 406.44

Molecular Weight (Monoisotopic): 406.1111

AlogP: 2.64

#Rotatable Bonds: 10

Polar Surface Area: 110.27

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -2.00

References

1. Zhao Q, Liu S, Li Y, Wang Q..  (2009)  Design, synthesis, and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole, or quinoline moieties.,  57  (7): [PMID:19271709] [10.1021/jf803632t]

Source

Source(1):

• Scientific Literature