4-amino-7-(4-chlorophenyl)-5-(2-phenyl-1H-indol-3-yl)-1H-pyrano[2,3-d]pyrimidin-2(5H)-one

ID: ALA2349113

PubChem CID: 71578524

Max Phase: Preclinical

Molecular Formula: C27H19ClN4O2

Molecular Weight: 466.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)[nH]c2c1C(c1c(-c3ccccc3)[nH]c3ccccc13)C=C(c1ccc(Cl)cc1)O2

Standard InChI:  InChI=1S/C27H19ClN4O2/c28-17-12-10-15(11-13-17)21-14-19(23-25(29)31-27(33)32-26(23)34-21)22-18-8-4-5-9-20(18)30-24(22)16-6-2-1-3-7-16/h1-14,19,30H,(H3,29,31,32,33)

Standard InChI Key:  DZAHBSXDHUOXHJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   19.2989  -24.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2989  -25.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0042  -25.6301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0042  -23.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5928  -25.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8842  -25.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1775  -25.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1783  -26.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8916  -26.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5953  -26.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0042  -23.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5923  -21.9234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3400  -22.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4095  -21.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6577  -22.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4521  -22.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9991  -22.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7462  -21.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9523  -21.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6353  -23.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9275  -22.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2201  -23.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2194  -23.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9319  -24.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6364  -23.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7095  -24.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7079  -25.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4121  -25.6311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4112  -24.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4093  -23.1848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1160  -24.4056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1222  -25.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4717  -26.8640    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.8315  -25.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  3  1  0
  3 27  1  0
 26  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2  5  1  0
  4 11  1  0
 11 15  1  0
 14 12  1  0
 12 13  1  0
 13 11  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 13 20  1  0
 26 27  2  0
 27 28  1  0
 28 32  1  0
 31 29  2  0
 29 26  1  0
 29 30  1  0
 31 32  1  0
  8 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2349113

   4-amino-7-(4-chlorophenyl)-5-(2-phenyl-1H-indol-3-yl)-1,5-dihydropyrano[2,3-d]pyrimidin-2-one

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: 466.93

Molecular Weight (Monoisotopic): 466.1197

AlogP: 5.72

#Rotatable Bonds: 3

Polar Surface Area: 96.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.26

CX Basic pKa: ┄

CX LogP: 4.52

CX LogD: 4.47

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -0.20

References

1. Saundane AR, Vijaykumar K, Vaijinath AV..  (2013)  Synthesis of novel 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents.,  23  (7): [PMID:23454016] [10.1016/j.bmcl.2013.02.036]

Source

Source(1):

• Scientific Literature