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

ID: ALA5284985

Max Phase: Preclinical

Molecular Formula: C21H19N5O3

Molecular Weight: 389.42

Names and Identifiers

Canonical SMILES:  Cc1ccc(Nc2nc(N)nc(COc3ccc4c(C)cc(=O)oc4c3)n2)cc1

Standard InChI:  InChI=1S/C21H19N5O3/c1-12-3-5-14(6-4-12)23-21-25-18(24-20(22)26-21)11-28-15-7-8-16-13(2)9-19(27)29-17(16)10-15/h3-10H,11H2,1-2H3,(H3,22,23,24,25,26)

Standard InChI Key:  FHNISROOMWHNPC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -2.8384    0.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2636    0.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2636    1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5519    2.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8384    1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5519    2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529   -0.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -0.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -1.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -2.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -2.8737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213   -1.6422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213   -0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0015   -0.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8449   -0.8151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5521   -0.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636   -0.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5521    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362    0.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1301   -0.4106    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
  5  7  1  0
  8  2  1  0
  9  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 26 24  1  0
 19 26  1  0
 26 27  2  0
 27 28  1  0
 28 17  2  0
 14 29  1  0
 29  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284985

   ---

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: 389.42

Molecular Weight (Monoisotopic): 389.1488

AlogP: 3.50

#Rotatable Bonds: 5

Polar Surface Area: 116.16

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.05

CX Basic pKa: 4.11

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.25

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