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

ID: ALA1087974

PubChem CID: 17271141

Max Phase: Preclinical

Molecular Formula: C23H26N4O3S

Molecular Weight: 438.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCn2c3c(c(=O)[nH]c2=S)CN(Cc2ccccc2)CN3)cc1OC

Standard InChI:  InChI=1S/C23H26N4O3S/c1-29-19-9-8-16(12-20(19)30-2)10-11-27-21-18(22(28)25-23(27)31)14-26(15-24-21)13-17-6-4-3-5-7-17/h3-9,12,24H,10-11,13-15H2,1-2H3,(H,25,28,31)

Standard InChI Key:  MPGYLBUVNALILU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.3147    0.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025    2.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025    1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169    0.9579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169    2.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3158    3.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0355    2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405    1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    0.9671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4694    1.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4604    2.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7431    2.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8880    0.9579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1702    2.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5991   -0.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969   -1.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8823   -1.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8797   -2.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936   -2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3116   -2.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -2.7459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508   -2.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -3.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8774   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8893    2.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8946    1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6128    0.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3236    1.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3116    2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5929    2.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  2  0
  3 13  2  0
 27 28  1  0
  4  1  1  0
 28 29  2  0
 11 14  1  0
 29 30  1  0
  2  3  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1087974

   6-Benzyl-1-[2-(3,4-dimethoxyphenyl)ethyl]-2-sulfanylidene-1H,2H,3H,4H,5H,6H,7H,8H-[1,3]diazino[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: 438.55

Molecular Weight (Monoisotopic): 438.1726

AlogP: 3.55

#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: 5.23

CX LogP: 3.37

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: -1.01

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