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

ID: ALA1088078

PubChem CID: 44246367

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)n2CCc2cc(OC)ccc2OC)C1

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

Standard InChI Key:  NYYQCSKFMQYOAZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.9609  -22.7562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609  -23.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6753  -23.9983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6753  -22.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741  -21.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741  -24.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3938  -22.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989  -23.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1157  -23.9891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8278  -23.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8188  -22.7418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015  -22.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880  -25.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869  -26.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700  -26.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685  -27.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829  -27.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004  -27.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984  -26.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463  -23.9983    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285  -22.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2476  -22.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9574  -22.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8118  -26.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5273  -26.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533  -27.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396  -27.2919    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
 16 26  1  0
  1  2  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088078

   1-[2-(2,5-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: -1.09

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