6-[(1-methyl-2,2-dioxido-1,3-dihydro-2,1-benzothiazol-5-yl)carbonyl]-2-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

ID: ALA4593073

PubChem CID: 155569120

Max Phase: Preclinical

Molecular Formula: C22H20N4O4S

Molecular Weight: 436.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1c2ccc(C(=O)N3CCc4nc(-c5ccccc5)[nH]c(=O)c4C3)cc2CS1(=O)=O

Standard InChI:  InChI=1S/C22H20N4O4S/c1-25-19-8-7-15(11-16(19)13-31(25,29)30)22(28)26-10-9-18-17(12-26)21(27)24-20(23-18)14-5-3-2-4-6-14/h2-8,11H,9-10,12-13H2,1H3,(H,23,24,27)

Standard InChI Key:  SIFOJXGOKNYARJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.5541  -19.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8483  -19.9799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.5586  -20.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8207  -20.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8195  -21.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5276  -22.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2372  -21.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2344  -20.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5258  -20.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9406  -20.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6471  -20.7863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6433  -19.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9330  -19.5623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6430  -18.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3523  -19.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3508  -20.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0558  -20.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7669  -20.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7684  -19.5636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0589  -19.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4773  -19.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1838  -19.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4796  -18.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1771  -20.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8828  -20.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8860  -19.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5923  -19.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5890  -20.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3659  -20.6419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3713  -19.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6162  -21.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  2  0
 10 13  1  0
 11 16  1  0
 15 12  1  0
 12 13  1  0
 12 14  2  0
 15 16  2  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 28  2  0
 27 26  2  0
 26 22  1  0
 27 28  1  0
 28 29  1  0
 29  2  1  0
  2 30  1  0
 30 27  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4593073

   ---

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: 436.49

Molecular Weight (Monoisotopic): 436.1205

AlogP: 1.92

#Rotatable Bonds: 2

Polar Surface Area: 103.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.98

CX Basic pKa: 0.58

CX LogP: 0.48

CX LogD: 0.40

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.66

Np Likeness Score: -1.41

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