4,6-Bis(benzylthio)-2-(methylthio)pyrimidine-5-carboxylic Acid

ID: ALA1172425

Cas Number: 883872-01-3

PubChem CID: 16040328

Max Phase: Preclinical

Molecular Formula: C20H18N2O2S3

Molecular Weight: 414.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(SCc2ccccc2)c(C(=O)O)c(SCc2ccccc2)n1

Standard InChI:  InChI=1S/C20H18N2O2S3/c1-25-20-21-17(26-12-14-8-4-2-5-9-14)16(19(23)24)18(22-20)27-13-15-10-6-3-7-11-15/h2-11H,12-13H2,1H3,(H,23,24)

Standard InChI Key:  JQFMWAZMMYZMOM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.6576   -8.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576   -9.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -9.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -9.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -8.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432  -10.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287  -11.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576  -11.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -7.5145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -7.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5142   -9.9895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9147   -9.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147  -10.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292  -11.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437  -10.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -9.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -9.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721   -9.9895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866   -9.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -9.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5155   -9.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -9.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300  -10.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5155  -11.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010  -10.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
 10 11  1  0
  1 10  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 12 13  1  0
  5 12  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 20 21  1  0
  3 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1172425

   4,6-Bis(benzylthio)-2-(methylthio)pyrimidine-5-carboxylic Acid

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: 414.58

Molecular Weight (Monoisotopic): 414.0530

AlogP: 5.48

#Rotatable Bonds: 8

Polar Surface Area: 63.08

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.70

CX Basic pKa: 0.62

CX LogP: 6.70

CX LogD: 3.39

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.30

Np Likeness Score: -0.93

References

1. Seto S, Okada K, Kiyota K, Isogai S, Iwago M, Shinozaki T, Kitamura Y, Kohno Y, Murakami K..  (2010)  Design, synthesis, and structure-activity relationship studies of novel 2,4,6-trisubstituted-5-pyrimidinecarboxylic acids as peroxisome proliferator-activated receptor gamma (PPARgamma) partial agonists with comparable antidiabetic efficacy to rosiglitazone.,  53  (13): [PMID:20527969] [10.1021/jm100443s]

Source

Source(1):

• Scientific Literature