(Z)-2-(2-((2-(2-(2-(3-(trifluoromethyl)phenylamino)thiazol-4-yl)acetyl)hydrazono)methyl)phenoxy)acetic acid

ID: ALA597777

PubChem CID: 5498424

Max Phase: Preclinical

Molecular Formula: C21H17F3N4O4S

Molecular Weight: 478.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 01078734 | CHEMBL597777|ZINC 01078734|BDBM50481425

Canonical SMILES:  O=C(O)COc1ccccc1/C=N\NC(=O)Cc1csc(Nc2cccc(C(F)(F)F)c2)n1

Standard InChI:  InChI=1S/C21H17F3N4O4S/c22-21(23,24)14-5-3-6-15(8-14)26-20-27-16(12-33-20)9-18(29)28-25-10-13-4-1-2-7-17(13)32-11-19(30)31/h1-8,10,12H,9,11H2,(H,26,27)(H,28,29)(H,30,31)/b25-10-

Standard InChI Key:  TZYCJQGYAOUYGY-MRUKODCESA-N

Molfile:  

     RDKit          2D

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   11.9822  -12.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8027  -12.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1383  -11.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8563  -12.1146    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7631  -12.8489    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5906  -11.2079    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9889  -10.3486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5040   -9.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6790   -9.6811    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4240   -8.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0915   -8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3770   -6.3491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -7.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -5.9366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -5.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3770   -4.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3770   -3.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8059   -3.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8059   -4.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0915   -3.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0915   -5.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -3.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9481   -3.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2336   -3.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2336   -2.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -3.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 12  2  0
  7  8  1  0
 15 17  1  0
 17 18  1  0
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 18 19  1  0
  4  5  1  0
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  2  3  1  0
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 27 25  2  0
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  1  7  1  0
 24 29  1  0
  3  4  2  0
 29 30  1  0
 13 14  1  0
 30 31  1  0
 14 15  2  0
 31 32  1  0
 15 16  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA597777

   2-[2-[(Z)-[[2-[2-[3-(trifluoromethyl)anilino]-1,3-thiazol-4-yl]acetyl]hydrazinylidene]methyl]phenoxy]acetic acid

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: 478.45

Molecular Weight (Monoisotopic): 478.0923

AlogP: 4.06

#Rotatable Bonds: 9

Polar Surface Area: 112.91

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: 2.53

CX LogP: 3.99

CX LogD: 0.89

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -2.31

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature