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

ID: ALA1087703

PubChem CID: 44246373

Max Phase: Preclinical

Molecular Formula: C19H26N4O3S

Molecular Weight: 390.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CNc2c(c(=O)[nH]c(=S)n2CCc2ccc(OC)cc2OC)C1

Standard InChI:  InChI=1S/C19H26N4O3S/c1-4-8-22-11-15-17(20-12-22)23(19(27)21-18(15)24)9-7-13-5-6-14(25-2)10-16(13)26-3/h5-6,10,20H,4,7-9,11-12H2,1-3H3,(H,21,24,27)

Standard InChI Key:  PPPAPJFPGQOYCE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.4400  -23.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4400  -23.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1544  -24.3787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1544  -22.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1533  -21.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1533  -25.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8730  -23.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8780  -23.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5948  -24.3695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3069  -23.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2979  -23.1223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5806  -22.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8672  -25.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8660  -26.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1492  -26.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1477  -27.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8622  -28.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5796  -27.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5775  -26.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7255  -24.3787    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0077  -22.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7268  -23.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4365  -22.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2910  -26.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0064  -26.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8621  -28.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1476  -29.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 13  1  0
  3  6  1  0
 13 14  1  0
  1  4  1  0
 14 15  2  0
  2  3  1  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  3  8  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 14  1  0
  7  4  1  0
  2 20  2  0
  9 10  1  0
 11 21  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
  4  5  2  0
 19 24  1  0
 11 12  1  0
 24 25  1  0
 12  7  1  0
 17 26  1  0
  1  2  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1087703

   1-[2-(2,4-dimethoxyphenyl)ethyl]-6-propyl-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: 390.51

Molecular Weight (Monoisotopic): 390.1726

AlogP: 2.76

#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: 5.74

CX LogP: 2.53

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.71

Np Likeness Score: -1.07

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, 

3. Asano, N N and 7 more authors.  2000-07  In vitro inhibition and intracellular enhancement of lysosomal alpha-galactosidase A activity in Fabry lymphoblasts by 1-deoxygalactonojirimycin and its derivatives.  [PMID:10866822]

4. Xiao, Jingbo and 17 more authors.  2012-09-13  Discovery of a novel noniminosugar acid α glucosidase chaperone series.  [PMID:22834902]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays