7-((4-amino-6-((1,3-dihydroisobenzofuran-5-yl)amino)-1,3,5-triazin-2-yl)methoxy)-4-methyl-2H-chromen-2-one

ID: ALA5285406

Max Phase: Preclinical

Molecular Formula: C22H19N5O4

Molecular Weight: 417.43

Names and Identifiers

Canonical SMILES:  Cc1cc(=O)oc2cc(OCc3nc(N)nc(Nc4ccc5c(c4)COC5)n3)ccc12

Standard InChI:  InChI=1S/C22H19N5O4/c1-12-6-20(28)31-18-8-16(4-5-17(12)18)30-11-19-25-21(23)27-22(26-19)24-15-3-2-13-9-29-10-14(13)7-15/h2-8H,9-11H2,1H3,(H3,23,24,25,26,27)

Standard InChI Key:  COJRHISJEWADDU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
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   -3.5706    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5696    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567    2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888    2.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3865    2.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706   -0.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557   -1.6914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389   -2.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389   -2.9253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -1.6877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -0.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0015   -0.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7166   -0.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468   -0.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591   -0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698   -0.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2848   -0.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559    0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559    1.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    0.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300    0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7166    0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -0.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  6  7  1  0
  7  8  1  0
  9  8  1  0
  5  9  1  0
 10  2  1  0
 11 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 28 26  1  0
 21 28  1  0
 28 29  2  0
 29 30  1  0
 30 19  2  0
 16 31  1  0
 31 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285406

   ---

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: 417.43

Molecular Weight (Monoisotopic): 417.1437

AlogP: 3.22

#Rotatable Bonds: 5

Polar Surface Area: 125.39

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.48

CX Basic pKa: 4.10

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.20

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