N-[4-(1,3-dioxoisoindolin-2-yl)-2,3,5-trifluorophenyl]-3-methylfuran-2-carboxamide

ID: ALA4742005

PubChem CID: 162645938

Max Phase: Preclinical

Molecular Formula: C20H11F3N2O4

Molecular Weight: 400.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccoc1C(=O)Nc1cc(F)c(N2C(=O)c3ccccc3C2=O)c(F)c1F

Standard InChI:  InChI=1S/C20H11F3N2O4/c1-9-6-7-29-17(9)18(26)24-13-8-12(21)16(15(23)14(13)22)25-19(27)10-4-2-3-5-11(10)20(25)28/h2-8H,1H3,(H,24,26)

Standard InChI Key:  OHYRNNUKSKXFBG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   14.9700  -11.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9689  -12.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6843  -13.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4014  -12.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3985  -11.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6825  -11.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1121  -11.3871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8652  -11.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1925  -10.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9990  -10.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4135  -11.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2346  -11.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6422  -10.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2269   -9.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4072   -9.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2535  -13.0453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5429  -12.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8275  -13.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5436  -11.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0729  -12.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5190  -13.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9330  -14.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7402  -13.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9025  -11.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5799  -10.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0378  -12.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6801  -10.5722    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2586  -11.3983    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.1125  -13.0452    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8 11  1  0
 10  9  1  0
  9  7  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  1  0
 20 24  1  0
  9 25  2  0
  8 26  2  0
  6 27  1  0
  1 28  1  0
  4 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4742005

   ---

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: 400.31

Molecular Weight (Monoisotopic): 400.0671

AlogP: 4.06

#Rotatable Bonds: 3

Polar Surface Area: 79.62

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.61

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.17

References

1. Davis DC,Bungard JD,Chang S,Rodriguez AL,Blobaum AL,Boutaud O,Melancon BJ,Niswender CM,Jeffrey Conn P,Lindsley CW.  (2021)  Lead optimization of the VU0486321 series of mGlu PAMs. Part 4: SAR reveals positive cooperativity across multiple mGlu receptor subtypes leading to subtype unselective PAMs.,  32  [PMID:33253881] [10.1016/j.bmcl.2020.127724]

Source

Source(1):

• Scientific Literature