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

ID: ALA2229422

PubChem CID: 42604296

Max Phase: Preclinical

Molecular Formula: C19H19F3N4O4S

Molecular Weight: 456.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H19F3N4O4S/c1-3-28-8-9-29-18(27)14(10-23)17(31-2)24-11-15-25-16(26-30-15)12-4-6-13(7-5-12)19(20,21)22/h4-7,24H,3,8-9,11H2,1-2H3/b17-14+

Standard InChI Key:  TVGIEEDEGHUKIB-SAPNQHFASA-N

Molfile:  

     RDKit          2D

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   36.9470  -12.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3555  -12.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3555  -11.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1727  -11.4387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9470  -10.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5813  -12.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3985  -12.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8071  -11.4387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6243  -11.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0329  -12.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.9038  -11.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.9211   -9.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   33.6174   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7365  -10.5658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8902   -9.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8576   -8.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1344   -8.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4433   -8.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4799   -9.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2035   -9.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7187   -8.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6838   -7.4267    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.0291   -8.6816    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.0050   -7.8335    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.7212  -12.8541    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.9040  -12.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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  3 12  3  0
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 24 25  2  0
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  1 30  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA2229422

   2-ethoxyethyl (E)-2-cyano-3-methylsulfanyl-3-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methylamino]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: 456.45

Molecular Weight (Monoisotopic): 456.1079

AlogP: 3.52

#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: 4.45

CX LogD: 4.45

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.25

Np Likeness Score: -1.85

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