1-(3,4-dimethoxyphenethyl)-6-isobutyl-2-thioxo-2,3,5,6,7,8-hexahydropyrimido[4,5-d]pyrimidin-4(1H)-one

ID: ALA1088509

PubChem CID: 44246396

Max Phase: Preclinical

Molecular Formula: C20H28N4O3S

Molecular Weight: 404.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCn2c3c(c(=O)[nH]c2=S)CN(CC(C)C)CN3)cc1OC

Standard InChI:  InChI=1S/C20H28N4O3S/c1-13(2)10-23-11-15-18(21-12-23)24(20(28)22-19(15)25)8-7-14-5-6-16(26-3)17(9-14)27-4/h5-6,9,13,21H,7-8,10-12H2,1-4H3,(H,22,25,28)

Standard InChI Key:  ZQZRSGVEEBFWSZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   13.0367  -22.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3246  -20.4279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3246  -21.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0391  -21.6700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0391  -20.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0378  -19.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7576  -20.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7626  -21.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4794  -21.6607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1915  -21.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1825  -20.4136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4652  -20.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6100  -21.6700    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8922  -19.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3212  -22.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3190  -23.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6043  -24.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6018  -24.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3157  -25.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0337  -24.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0327  -24.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8860  -25.3738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1729  -24.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3145  -26.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995  -26.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6113  -20.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3211  -19.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6207  -21.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
 11 14  1  0
  2  3  1  0
  1 15  1  0
  2  5  1  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  3  4  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  8  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 21 16  1  0
  7  5  1  0
 18 22  1  0
 10 11  1  0
 22 23  1  0
 19 24  1  0
 11 12  1  0
 24 25  1  0
 12  7  1  0
 14 26  1  0
  5  6  2  0
 26 27  1  0
  3 13  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088509

   1-[2-(3,4-dimethoxyphenyl)ethyl]-6-(2-methylpropyl)-2-sulfanylidene-7,8-dihydro-5H-pyrimido[4,5-d]pyrimidin-4-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: 404.54

Molecular Weight (Monoisotopic): 404.1882

AlogP: 3.01

#Rotatable Bonds: 7

Polar Surface Area: 71.52

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.89

CX Basic pKa: 6.05

CX LogP: 2.79

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -0.96

References

1. Marugan JJ, Zheng W, Motabar O, Southall N, Goldin E, Sidransky E, Aungst RA, Liu K, Sadhukhan SK, Austin CP..  (2010)  Evaluation of 2-thioxo-2,3,5,6,7,8-hexahydropyrimido[4,5-d]pyrimidin-4(1H)-one analogues as GAA activators.,  45  (5): [PMID:20206419] [10.1016/j.ejmech.2010.01.027]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays