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

ID: ALA4453480

PubChem CID: 155523113

Max Phase: Preclinical

Molecular Formula: C22H19N3O4

Molecular Weight: 389.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(C(=O)N2CCc3nc(-c4ccccc4)[nH]c(=O)c3C2)cc1

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

Standard InChI Key:  IIFXOEHKSRCLRR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   26.5078  -20.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5066  -21.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2147  -21.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9243  -21.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9215  -20.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2129  -20.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6277  -20.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3342  -20.5097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3304  -18.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6201  -19.2858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3301  -18.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0394  -19.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0379  -20.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7429  -20.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4540  -20.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4555  -19.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7460  -18.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1644  -18.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8709  -19.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1667  -18.0633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8642  -20.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5699  -20.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5731  -18.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2794  -19.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2761  -20.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9834  -20.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9828  -21.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6915  -20.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3989  -20.5197    0.0000 C   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
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4453480

   ---

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: 2.42

#Rotatable Bonds: 3

Polar Surface Area: 92.36

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.98

CX Basic pKa: 0.65

CX LogP: 1.99

CX LogD: 1.90

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.19

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]

2. Eadsforth, Thomas C and 13 more authors.  2015-10-22  Characterization of 2,4-Diamino-6-oxo-1,6-dihydropyrimidin-5-yl Ureido Based Inhibitors of Trypanosoma brucei FolD and Testing for Antiparasitic Activity.  [PMID:26322631]

Source

Source(1):

• Scientific Literature