4-(3,4-dihydroxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acidethyl ester

ID: ALA393502

Chembl Id: CHEMBL393502

PubChem CID: 2831304

Max Phase: Preclinical

Molecular Formula: C14H16N2O4S

Molecular Weight: 308.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=S)NC1c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C14H16N2O4S/c1-3-20-13(19)11-7(2)15-14(21)16-12(11)8-4-5-9(17)10(18)6-8/h4-6,12,17-18H,3H2,1-2H3,(H2,15,16,21)

Standard InChI Key:  JRBBYQDOWHPACZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA393502

   Ethyl 4-(3,4-dihydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

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: 308.36

Molecular Weight (Monoisotopic): 308.0831

AlogP: 1.45

#Rotatable Bonds: 3

Polar Surface Area: 90.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: ┄

CX LogP: 1.52

CX LogD: 1.52

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.38

Np Likeness Score: -0.57

References

1. Klein E, DeBonis S, Thiede B, Skoufias DA, Kozielski F, Lebeau L..  (2007)  New chemical tools for investigating human mitotic kinesin Eg5.,  15  (19): [PMID:17587586] [10.1016/j.bmc.2007.06.016]

2. da Silva DL, Reis FS, Muniz DR, Ruiz AL, de Carvalho JE, Sabino AA, Modolo LV, de Fátima A..  (2012)  Free radical scavenging and antiproliferative properties of Biginelli adducts.,  20  (8): [PMID:22410248] [10.1016/j.bmc.2012.02.036]

3. Damgaard M, Al-Khawaja A, Nittegaard-Nielsen M, Petersen RF, Wellendorph P, Frølund B..  (2017)  Monastrol, a 3,4-dihydropyrimidin-2(1H)-thione, as structural scaffold for the development of modulators for GHB high-affinity binding sites and α1β2δ GABAA receptors.,  138  [PMID:28683403] [10.1016/j.ejmech.2017.06.024]

Source

Source(1):

• Scientific Literature