6-amino-2-(2-(1-(benzo[d][1,3]dioxol-5-ylmethyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-oxoethylthio)pyrimidin-4(3H)-one

ID: ALA596747

PubChem CID: 135427418

Max Phase: Preclinical

Molecular Formula: C20H20N4O4S

Molecular Weight: 412.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 02642996

Canonical SMILES:  Cc1cc(C(=O)CSc2nc(N)cc(=O)[nH]2)c(C)n1Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C20H20N4O4S/c1-11-5-14(15(25)9-29-20-22-18(21)7-19(26)23-20)12(2)24(11)8-13-3-4-16-17(6-13)28-10-27-16/h3-7H,8-10H2,1-2H3,(H3,21,22,23,26)

Standard InChI Key:  CZIRSEVSHBGBIZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    6.2614    3.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9759    3.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9759    2.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614    1.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5470    3.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5470    2.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623    2.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2774    2.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623    3.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6904    1.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6904    1.1045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0229    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2779   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1029   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3578    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1424    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2383    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878   -0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2522   -1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4083   -0.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7372   -2.2536    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4016   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8865   -3.6747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -4.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7305   -4.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2456   -3.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5811   -3.0935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0359   -5.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -3.9335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  3  4  2  0
 15 16  1  0
  6  7  1  0
 12 17  1  0
  7  8  1  0
 14 18  1  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 18 20  2  0
  4  6  1  0
 19 21  1  0
  3 10  1  0
 21 22  1  0
 22 23  1  0
  5  6  2  0
 10 11  1  0
 11 12  1  0
  1  2  2  0
  5  1  1  0
 22 27  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
  2  3  1  0
 24 28  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA596747

   ---

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: 412.47

Molecular Weight (Monoisotopic): 412.1205

AlogP: 2.52

#Rotatable Bonds: 6

Polar Surface Area: 112.23

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.62

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: -1.75

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature