2-(3-(2-cyanovinyl)phenoxy)-4-(4-(methylthio)pyrimidin-2-ylamino)benzonitrile

ID: ALA4536318

PubChem CID: 56599459

Max Phase: Preclinical

Molecular Formula: C21H15N5OS

Molecular Weight: 385.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSc1ccnc(Nc2ccc(C#N)c(Oc3cccc(/C=C/C#N)c3)c2)n1

Standard InChI:  InChI=1S/C21H15N5OS/c1-28-20-9-11-24-21(26-20)25-17-8-7-16(14-23)19(13-17)27-18-6-2-4-15(12-18)5-3-10-22/h2-9,11-13H,1H3,(H,24,25,26)/b5-3+

Standard InChI Key:  SSQAOFHSLQYKTC-HWKANZROSA-N

Molfile:  

 
     RDKit          2D

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   14.5212  -10.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2292  -11.3402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9389  -10.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9360  -10.1081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2274   -9.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2265   -8.8913    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5175   -8.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6472  -11.3382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3543  -10.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0593  -11.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7659  -10.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7650  -10.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0517   -9.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3481  -10.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0476   -8.8849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7532   -8.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4599   -8.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1650   -8.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1613   -7.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4465   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7443   -7.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4662   -9.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1727   -9.2863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4395   -6.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1436   -6.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1366   -5.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1268   -4.3818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  6  2  0
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  9 10  1  0
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 17 18  2  0
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 22 17  1  0
 23 24  3  0
 13 23  1  0
 21 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536318

   2-[3-[(E)-2-cyanovinyl]phenoxy]-4-[(4-methylsulfanylpyrimidin-2-yl)amino]benzonitrile

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 385.45

Molecular Weight (Monoisotopic): 385.0997

AlogP: 5.14

#Rotatable Bonds: 6

Polar Surface Area: 94.62

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.76

CX Basic pKa: 2.01

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -1.18

References

1. Jorgensen WL..  (2016)  Computer-aided discovery of anti-HIV agents.,  24  (20): [PMID:27485603] [10.1016/j.bmc.2016.07.039]

Source

Source(1):

• Scientific Literature