1-(3-((4-amino-6-((3-chloro-4-methylphenyl)amino)-1,3,5-triazin-2-yl)methoxy)-5-methoxyphenyl)pyrrolidin-2-one

ID: ALA5287642

Max Phase: Preclinical

Molecular Formula: C22H23ClN6O3

Molecular Weight: 454.92

Names and Identifiers

Canonical SMILES:  COc1cc(OCc2nc(N)nc(Nc3ccc(C)c(Cl)c3)n2)cc(N2CCCC2=O)c1

Standard InChI:  InChI=1S/C22H23ClN6O3/c1-13-5-6-14(8-18(13)23)25-22-27-19(26-21(24)28-22)12-32-17-10-15(9-16(11-17)31-2)29-7-3-4-20(29)30/h5-6,8-11H,3-4,7,12H2,1-2H3,(H3,24,25,26,27,28)

Standard InChI Key:  HGIMTNAGLPWSHB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -4.5947   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8801   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947   -1.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3093   -1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    0.0002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120   -1.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -1.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223   -2.4744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4025    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171   -0.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8321    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2598    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495   -0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9760   -0.4097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6906    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3093   -0.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9786   -1.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1545   -1.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5709   -1.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3093   -0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5449    2.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302    2.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  3  8  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
 24 22  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 28 27  1  0
 24 28  1  0
 28 29  2  0
  1 30  1  0
 20 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287642

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.92

Molecular Weight (Monoisotopic): 454.1520

AlogP: 3.87

#Rotatable Bonds: 7

Polar Surface Area: 115.49

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.66

CX Basic pKa: 4.08

CX LogP: 3.79

CX LogD: 3.79

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -1.76

References

1. Lückmann M, Shenol A, Nissen TAD, Petersen JE, Kouvchinov D, Schwartz TW, Frimurer TM..  (2022)  Optimization of First-in-Class Dual-Acting FFAR1/FFAR4 Allosteric Modulators with Novel Mode of Action.,  13  (12.0): [PMID:36518697] [10.1021/acsmedchemlett.2c00160]

Source

Source(1):

• Scientific Literature