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

ID: ALA5287009

Max Phase: Preclinical

Molecular Formula: C23H26N6O2

Molecular Weight: 418.50

Names and Identifiers

Canonical SMILES:  Cc1cc(OCc2nc(N)nc(NCCc3ccccc3)n2)cc(N2CCCC2=O)c1

Standard InChI:  InChI=1S/C23H26N6O2/c1-16-12-18(29-11-5-8-21(29)30)14-19(13-16)31-15-20-26-22(24)28-23(27-20)25-10-9-17-6-3-2-4-7-17/h2-4,6-7,12-14H,5,8-11,15H2,1H3,(H3,24,25,26,27,28)

Standard InChI Key:  VDEBVCJTQUJQJZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.6666   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9521    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9502   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6666   -1.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0962    0.2066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -1.0309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -1.0346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650   -2.2681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7598    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4745   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9022    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170    1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6186    0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333   -0.2034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6666   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5118   -1.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9283   -1.5879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9022    2.2681    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
  1  6  1  0
  6  5  2  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 10 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 25 23  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 28  1  0
 29 30  2  0
 21 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287009

   ---

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: 418.50

Molecular Weight (Monoisotopic): 418.2117

AlogP: 3.12

#Rotatable Bonds: 8

Polar Surface Area: 106.26

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.18

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.52

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