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

ID: ALA4795139

PubChem CID: 162672655

Max Phase: Preclinical

Molecular Formula: C20H18FN3O3S

Molecular Weight: 399.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(C(=O)Nc2cc(F)c(N3C(=O)C4=C(CCCC4)C3=O)cc2C)cs1

Standard InChI:  InChI=1S/C20H18FN3O3S/c1-10-7-17(24-19(26)12-5-3-4-6-13(12)20(24)27)14(21)8-15(10)23-18(25)16-9-28-11(2)22-16/h7-9H,3-6H2,1-2H3,(H,23,25)

Standard InChI Key:  VVMKCGXINVQJFF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   28.1669  -11.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1658  -12.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8779  -12.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5917  -12.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5889  -11.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8762  -11.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8737  -10.2517    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.4536  -12.7177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7421  -12.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0299  -12.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7427  -11.4831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2830  -12.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7357  -12.9928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.1437  -13.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9473  -13.5356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2946  -11.0662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0407  -11.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3738  -10.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1723  -10.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5829  -10.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3975  -10.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8024  -10.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3868   -9.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5736   -9.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7632   -9.7128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2135  -12.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8777  -13.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8095  -14.4507    0.0000 C   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
  2  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  5 16  1  0
 16 17  1  0
 17 20  1  0
 19 18  1  0
 18 16  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 18 25  2  0
 17 26  2  0
  3 27  1  0
 14 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4795139

   ---

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: 399.45

Molecular Weight (Monoisotopic): 399.1053

AlogP: 3.90

#Rotatable Bonds: 3

Polar Surface Area: 79.37

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 1.11

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.79

Np Likeness Score: -1.48

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