5-ethyl-2-mercapto-3H-pyrano[2,3-d]pyrimidine-4,7-dione

ID: ALA1672755

PubChem CID: 53322689

Max Phase: Preclinical

Molecular Formula: C9H8N2O3S

Molecular Weight: 224.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(=O)oc2nc(S)[nH]c(=O)c12

Standard InChI:  InChI=1S/C9H8N2O3S/c1-2-4-3-5(12)14-8-6(4)7(13)10-9(15)11-8/h3H,2H2,1H3,(H2,10,11,13,15)

Standard InChI Key:  AGWCOWNJAYMSIC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   -4.4928    2.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4940    1.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791    1.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809    3.0251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0657    2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0649    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347    1.7930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394    2.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552    3.0301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3479    0.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772    0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4907    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073    3.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    3.0397    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  7  8  1  0
  5  4  1  0
  8  9  1  0
  4  1  1  0
  9 10  2  0
 10  5  1  0
  7 11  2  0
  2  3  2  0
  3 12  1  0
  5  6  2  0
 12 13  1  0
  3  6  1  0
  1 14  2  0
  6  7  1  0
  9 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1672755

   5-ethyl-2-mercapto-3H-pyrano[2,3-d]pyrimidine-4,7-dione

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: 224.24

Molecular Weight (Monoisotopic): 224.0256

AlogP: 0.73

#Rotatable Bonds: 1

Polar Surface Area: 75.96

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.43

CX Basic pKa: ┄

CX LogP: 1.40

CX LogD: 0.60

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.55

Np Likeness Score: -0.82

References

1. Qin J, Rao A, Chen X, Zhu X, Liu Z, Huang X, Degrado S, Huang Y, Xiao D, Aslanian R, Cheewatrakoolpong B, Zhang H, Greenfeder S, Farley C, Cook J, Kurowski S, Li Q, van Heek M, Chintala M, Wang G, Hsieh Y, Li F, Palani A..  (2011)  Discovery of a potent nicotinic Acid receptor agonist for the treatment of dyslipidemia.,  2  (2): [PMID:24900295] [10.1021/ml100251u]

2. Huang X, Su J, Rao AU, Tang H, Zhou W, Zhu X, Chen X, Liu Z, Huang Y, Degrado S, Xiao D, Qin J, Aslanian R, McKittrick BA, Greenfeder S, Heek Mv, Chintala M, Palani A..  (2012)  SAR studies of C2 ethers of 2H-pyrano[2,3-d]pyrimidine-2,4,7(1H,3H)-triones as nicotinic acid receptor (NAR) agonist.,  22  (2): [PMID:22209457] [10.1016/j.bmcl.2011.12.041]

3. Elattar KM, El-Khateeb AY, Hamed SE..  (2022)  Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs.,  13  (5.0): [PMID:35694689] [10.1039/d2md00076h]

Source

Source(1):

• Scientific Literature