N-[4-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-5-fluoro-2-methylphenyl]-3-methylfuran-2-carboxamide

ID: ALA4792152

PubChem CID: 162670460

Max Phase: Preclinical

Molecular Formula: C21H19FN2O4

Molecular Weight: 382.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1NC(=O)c1occc1C

Standard InChI:  InChI=1S/C21H19FN2O4/c1-11-7-8-28-18(11)19(25)23-16-10-15(22)17(9-12(16)2)24-20(26)13-5-3-4-6-14(13)21(24)27/h7-10H,3-6H2,1-2H3,(H,23,25)

Standard InChI Key:  FDPGXFCCOLEURD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   15.8828  -19.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8816  -19.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5965  -20.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3129  -19.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3101  -19.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5947  -18.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5922  -17.8298    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.5963  -21.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1668  -20.3070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4526  -19.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7378  -20.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4533  -19.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9877  -19.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4352  -20.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8472  -21.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6543  -21.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8165  -19.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0231  -18.6488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7777  -18.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1059  -17.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9121  -17.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3260  -18.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1462  -18.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5588  -17.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1450  -16.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3185  -16.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4904  -17.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9536  -19.7850    0.0000 O   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
  6  7  1  0
  3  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 11  1  0
 13 17  1  0
  5 18  1  0
 18 19  1  0
 19 22  1  0
 21 20  1  0
 20 18  1  0
 21 22  2  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 20 27  2  0
 19 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4792152

   ---

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: 382.39

Molecular Weight (Monoisotopic): 382.1329

AlogP: 4.03

#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: 13.82

CX Basic pKa: 1.03

CX LogP: 3.78

CX LogD: 3.78

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.81

Np Likeness Score: -1.07

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