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

ID: ALA1087956

PubChem CID: 46889088

Max Phase: Preclinical

Molecular Formula: C20H28N4O3S

Molecular Weight: 404.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CNc2c(c(=O)[nH]c(=S)n2Cc2ccc(OCC)c(OCC)c2)C1

Standard InChI:  InChI=1S/C20H28N4O3S/c1-4-9-23-12-15-18(21-13-23)24(20(28)22-19(15)25)11-14-7-8-16(26-5-2)17(10-14)27-6-3/h7-8,10,21H,4-6,9,11-13H2,1-3H3,(H,22,25,28)

Standard InChI Key:  OGJGBMJTYZNTDD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.9471   -7.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -8.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182   -7.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8132   -8.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -9.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582   -9.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603   -9.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -9.5015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4016   -9.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5785  -10.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744  -10.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948  -11.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -8.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -5.7244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2349   -6.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493   -6.9664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493   -5.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9482   -4.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6678   -5.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6728   -6.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3896   -6.9572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1017   -6.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0927   -5.7100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3754   -5.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5204   -6.9664    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8025   -5.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5215   -5.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2312   -5.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  7  2  1  0
  3  4  1  0
  5  8  1  0
 14 17  1  0
 15 16  1  0
 16 20  1  0
 19 17  1  0
 17 18  2  0
 16  1  1  0
  8  9  1  0
  4  5  2  0
 19 20  2  0
  6 10  1  0
 20 21  1  0
  2  3  2  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  1  0
 23 24  1  0
 24 19  1  0
 11 12  1  0
 15 25  2  0
  1  2  1  0
 23 26  1  0
  9 13  1  0
 26 27  1  0
 14 15  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1087956

   1-[(3,4-diethoxyphenyl)methyl]-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: 404.54

Molecular Weight (Monoisotopic): 404.1882

AlogP: 3.35

#Rotatable Bonds: 8

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: 7.88

CX Basic pKa: 5.75

CX LogP: 2.95

CX LogD: 2.82

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.36

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. 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]

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

Source

Source(1):

• Scientific Literature