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

ID: ALA1088508

PubChem CID: 44246387

Max Phase: Preclinical

Molecular Formula: C17H22N4O3S

Molecular Weight: 362.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H22N4O3S/c1-20-9-12-15(18-10-20)21(17(25)19-16(12)22)7-6-11-4-5-13(23-2)14(8-11)24-3/h4-5,8,18H,6-7,9-10H2,1-3H3,(H,19,22,25)

Standard InChI Key:  UCAIRVAHANJBTH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.9739  -22.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616  -20.7763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616  -21.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762  -22.0184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762  -20.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750  -19.5341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6947  -20.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6998  -21.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4164  -22.0091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1287  -21.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1195  -20.7619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4022  -20.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472  -22.0184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8294  -20.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583  -23.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2560  -24.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5415  -24.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389  -25.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527  -25.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707  -25.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9698  -24.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8231  -25.7222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099  -25.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516  -26.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5366  -26.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  7  1  0
  5  6  2  0
  3 13  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA1088508

   1-[2-(3,4-dimethoxyphenyl)ethyl]-6-methyl-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: 362.46

Molecular Weight (Monoisotopic): 362.1413

AlogP: 1.98

#Rotatable Bonds: 5

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: 5.18

CX LogP: 1.65

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.79

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