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

ID: ALA4777502

PubChem CID: 162643634

Max Phase: Preclinical

Molecular Formula: C22H17FN2O4

Molecular Weight: 392.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)C(=O)N(c1cc(C)c(NC(=O)c3occc3C)cc1F)C2=O

Standard InChI:  InChI=1S/C22H17FN2O4/c1-11-4-5-14-15(8-11)22(28)25(21(14)27)18-9-13(3)17(10-16(18)23)24-20(26)19-12(2)6-7-29-19/h4-10H,1-3H3,(H,24,26)

Standard InChI Key:  LGXWAHSPYKIIOF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.9371  -28.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6492  -29.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3630  -28.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3602  -28.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6475  -27.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6450  -26.8886    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.6490  -30.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -29.3546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5134  -28.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8012  -29.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5140  -28.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0543  -29.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5070  -29.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9150  -30.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7186  -30.1725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8846  -28.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0705  -27.7039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8220  -28.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1525  -26.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9552  -26.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3651  -27.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1817  -27.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5945  -26.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1805  -25.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3577  -25.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5388  -26.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9963  -28.8335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5925  -25.2866    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
  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
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 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  2  0
 24 25  1  0
 25 26  2  0
 20 27  2  0
 19 28  2  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777502

   ---

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: 392.39

Molecular Weight (Monoisotopic): 392.1172

AlogP: 4.40

#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: ┄

CX LogP: 4.41

CX LogD: 4.41

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.44

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