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

ID: ALA4470717

PubChem CID: 155534669

Max Phase: Preclinical

Molecular Formula: C21H18N4O4

Molecular Weight: 390.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1cc(C(=O)N2CCc3nc(-c4ccccc4)[nH]c(=O)c3C2)ccc1C(=O)O

Standard InChI:  InChI=1S/C21H18N4O4/c22-16-10-13(6-7-14(16)21(28)29)20(27)25-9-8-17-15(11-25)19(26)24-18(23-17)12-4-2-1-3-5-12/h1-7,10H,8-9,11,22H2,(H,28,29)(H,23,24,26)

Standard InChI Key:  DOORXLPCOWHXNS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    1.8228  -14.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217  -15.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297  -15.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394  -15.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2365  -14.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5279  -14.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427  -14.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6493  -14.4468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6454  -12.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352  -13.2229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6451  -11.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3545  -13.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3530  -14.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0580  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690  -14.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706  -13.2241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0610  -12.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4794  -12.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1860  -13.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4818  -12.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792  -14.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8849  -14.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8882  -12.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5945  -13.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5911  -14.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2985  -14.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2940  -15.2717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0075  -14.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3028  -12.8210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  7 10  1  0
  8 13  1  0
 12  9  1  0
  9 10  1  0
  9 11  2  0
 12 13  2  0
 12 17  1  0
 13 14  1  0
 14 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
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4470717

   ---

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: 390.40

Molecular Weight (Monoisotopic): 390.1328

AlogP: 1.92

#Rotatable Bonds: 3

Polar Surface Area: 129.38

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.43

CX Basic pKa: 1.19

CX LogP: 1.46

CX LogD: -1.52

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -1.15

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