4-[(3-methyl-4-oxo-2-phenyl-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-6(4H)-yl)carbonyl]benzoic acid

ID: ALA4440948

PubChem CID: 155514741

Max Phase: Preclinical

Molecular Formula: C22H19N3O4

Molecular Weight: 389.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(-c2ccccc2)nc2c(c1=O)CN(C(=O)c1ccc(C(=O)O)cc1)CC2

Standard InChI:  InChI=1S/C22H19N3O4/c1-24-19(14-5-3-2-4-6-14)23-18-11-12-25(13-17(18)21(24)27)20(26)15-7-9-16(10-8-15)22(28)29/h2-10H,11-13H2,1H3,(H,28,29)

Standard InChI Key:  MLEXZDDSAFOKBW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   15.9600   -3.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7282   -3.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7270   -4.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4351   -4.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1447   -4.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1419   -3.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4333   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8481   -3.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5546   -3.6252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5507   -1.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8405   -2.4013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5505   -1.1746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2598   -2.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2583   -3.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6744   -3.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6759   -2.4025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9664   -1.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3848   -1.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0913   -2.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3871   -1.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0846   -3.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7903   -3.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7935   -2.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4998   -2.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4965   -3.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2038   -3.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2032   -4.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9119   -3.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1311   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  2  0
  8 11  1  0
  9 14  1  0
 13 10  1  0
 10 11  1  0
 10 12  2  0
 13 14  2  0
 13 17  1  0
 14  1  1  0
  1 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 25  2  0
 24 23  2  0
 23 19  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 11 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4440948

   ---

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: 389.41

Molecular Weight (Monoisotopic): 389.1376

AlogP: 2.34

#Rotatable Bonds: 3

Polar Surface Area: 92.50

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: 0.77

CX LogP: 1.86

CX LogD: -1.42

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -1.05

References

1. Kawai J, Ota M, Ohki H, Toki T, Suzuki M, Shimada T, Matsui S, Inoue H, Sugihara C, Matsuhashi N, Matsui Y, Takaishi S, Nakayama K..  (2019)  Structure-Based Design and Synthesis of an Isozyme-Selective MTHFD2 Inhibitor with a Tricyclic Coumarin Scaffold.,  10  (6): [PMID:31223444] [10.1021/acsmedchemlett.9b00069]

Source

Source(1):

• Scientific Literature