2-ethoxyethyl 2-cyano-3-((3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)methylamino)pent-2-enoate

ID: ALA2229426

PubChem CID: 42604423

Max Phase: Preclinical

Molecular Formula: C19H21FN4O4

Molecular Weight: 388.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H21FN4O4/c1-3-16(15(11-21)19(25)27-10-9-26-4-2)22-12-17-23-18(24-28-17)13-5-7-14(20)8-6-13/h5-8,22H,3-4,9-10,12H2,1-2H3/b16-15-

Standard InChI Key:  TVUMODINAPCUGO-NXVVXOECSA-N

Molfile:  

     RDKit          2D

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   36.3815  -17.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7901  -17.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7901  -16.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6073  -16.3501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3815  -15.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0159  -17.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8331  -17.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2417  -16.3501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   37.2006  -18.4722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1557  -16.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3384  -16.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9754  -15.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3557  -14.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7842  -14.3058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0520  -14.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1711  -15.4772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3247  -14.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2922  -13.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5690  -13.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8778  -13.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9145  -14.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6381  -14.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1533  -13.1545    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.1557  -17.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3385  -17.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 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:

   

   ALA2229426

   2-ethoxyethyl (Z)-2-cyano-3-[[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]methylamino]pent-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: 388.40

Molecular Weight (Monoisotopic): 388.1547

AlogP: 2.73

#Rotatable Bonds: 10

Polar Surface Area: 110.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: -1.91

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