(R)-(-)-7-amino-1-(2,5-dimethoxyphenyl)-3-propylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

ID: ALA4082465

PubChem CID: 21198161

Max Phase: Preclinical

Molecular Formula: C18H20N4O4

Molecular Weight: 356.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2ccc(N)nc2n(-c2cc(OC)ccc2OC)c1=O

Standard InChI:  InChI=1S/C18H20N4O4/c1-4-9-21-17(23)12-6-8-15(19)20-16(12)22(18(21)24)13-10-11(25-2)5-7-14(13)26-3/h5-8,10H,4,9H2,1-3H3,(H2,19,20)

Standard InChI Key:  QGEIKWQJVMRYIN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.6016  -13.0331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016  -13.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3149  -14.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3149  -12.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0281  -13.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0265  -13.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7386  -14.2665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4528  -13.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4505  -13.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7378  -12.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1647  -14.2674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8866  -14.2707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3149  -11.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8847  -12.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703  -13.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4576  -12.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3150  -15.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5983  -15.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5992  -16.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3159  -16.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0333  -16.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290  -15.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8824  -15.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1670  -15.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7510  -16.7312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7552  -17.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  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
  8 11  1  0
  2 12  2  0
  4 13  2  0
  1 14  1  0
 14 15  1  0
 15 16  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
  3 17  1  0
 18 23  1  0
 23 24  1  0
 21 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4082465

   7-Amino-1-(2,5-dimethoxyphenyl)-3-propylpyrido[2,3-d]pyrimidine-2,4-dione

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: 356.38

Molecular Weight (Monoisotopic): 356.1485

AlogP: 1.56

#Rotatable Bonds: 5

Polar Surface Area: 101.37

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.10

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -0.87

References

1. Hasegawa F, Kawamura K, Tsuchikawa H, Murata M..  (2017)  Stable C-N axial chirality in 1-aryluracil scaffold and differences in in vitro metabolic clearance between atropisomers of PDE4 inhibitor.,  25  (16): [PMID:28698053] [10.1016/j.bmc.2017.06.042]

2. Hasegawa F, Kawamura K, Tsuchikawa H, Murata M..  (2017)  Stable C-N axial chirality in 1-aryluracil scaffold and differences in in vitro metabolic clearance between atropisomers of PDE4 inhibitor.,  25  (16): [PMID:28698053] [10.1016/j.bmc.2017.06.042]

Source

Source(1):

• Scientific Literature