3-Methyl-2-(8-methyl-2-oxo-3-(thiophen-2-yl)-2H-chromen-6-yl)-2,3-dihydroquinazolin-4(1h)-one

ID: ALA4167588

PubChem CID: 145954324

Max Phase: Preclinical

Molecular Formula: C23H18N2O3S

Molecular Weight: 402.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C2Nc3ccccc3C(=O)N2C)cc2cc(-c3cccs3)c(=O)oc12

Standard InChI:  InChI=1S/C23H18N2O3S/c1-13-10-15(21-24-18-7-4-3-6-16(18)22(26)25(21)2)11-14-12-17(19-8-5-9-29-19)23(27)28-20(13)14/h3-12,21,24H,1-2H3

Standard InChI Key:  RPVJSBOBODJWGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   18.0882   -2.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0871   -3.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7951   -3.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7933   -1.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5020   -2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5008   -3.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2070   -3.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9189   -3.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9200   -2.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2093   -1.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6253   -3.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6287   -1.8532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3826   -3.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6754   -3.0757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9694   -3.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3839   -4.3029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6718   -4.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9688   -4.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2622   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2575   -5.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9653   -5.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6689   -5.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6780   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2626   -3.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7909   -1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7111   -4.2950    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.5086   -4.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9154   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3691   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
  9 12  2  0
 13 14  1  0
 13 16  1  0
 14 15  1  0
 15 18  1  0
 17 16  1  0
  2 13  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 23  1  0
 15 24  2  0
  4 25  1  0
 11 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4167588

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 402.48

Molecular Weight (Monoisotopic): 402.1038

AlogP: 5.03

#Rotatable Bonds: 2

Polar Surface Area: 62.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.47

CX Basic pKa: ┄

CX LogP: 5.18

CX LogD: 5.18

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -0.80

References

1. Singh LR, Kumar A, Upadhyay A, Gupta S, Palanati GR, Sikka K, Siddiqi MI, Yadav PN, Sashidhara KV..  (2018)  Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy.,  152  [PMID:29709786] [10.1016/j.ejmech.2018.04.037]

Source

Source(1):

• Scientific Literature