5,6-Dihydroxy-2-thiophen-2-yl-pyrimidine-4-carboxylic acid methyl ester

ID: ALA187010

Chembl Id: CHEMBL187010

PubChem CID: 135446971

Max Phase: Preclinical

Molecular Formula: C10H8N2O4S

Molecular Weight: 252.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1nc(-c2cccs2)nc(O)c1O

Standard InChI:  InChI=1S/C10H8N2O4S/c1-16-10(15)6-7(13)9(14)12-8(11-6)5-3-2-4-17-5/h2-4,13H,1H3,(H,11,12,14)

Standard InChI Key:  QAIMSDCSXBBWEK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA187010

   ---

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: 252.25

Molecular Weight (Monoisotopic): 252.0205

AlogP: 1.40

#Rotatable Bonds: 2

Polar Surface Area: 92.54

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.92

CX Basic pKa: 0.36

CX LogP: 2.80

CX LogD: 2.79

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.78

Np Likeness Score: -1.36

References

1. Stansfield I, Avolio S, Colarusso S, Gennari N, Narjes F, Pacini B, Ponzi S, Harper S..  (2004)  Active site inhibitors of HCV NS5B polymerase. The development and pharmacophore of 2-thienyl-5,6-dihydroxypyrimidine-4-carboxylic acid.,  14  (20): [PMID:15380204] [10.1016/j.bmcl.2004.07.075]

2. Chapman TM, Wallace C, Gillen KJ, Bakrania P, Khurana P, Coombs PJ, Fox S, Bureau EA, Brownlees J, Melton DW, Saxty B..  (2015)  N-Hydroxyimides and hydroxypyrimidinones as inhibitors of the DNA repair complex ERCC1-XPF.,  25  (19): [PMID:26321360] [10.1016/j.bmcl.2015.08.024]

3. He T, Edwards TC, Xie J, Aihara H, Geraghty RJ, Wang Z..  (2022)  4,5-Dihydroxypyrimidine Methyl Carboxylates, Carboxylic Acids, and Carboxamides as Inhibitors of Human Cytomegalovirus pUL89 Endonuclease.,  65  (7.0): [PMID:35377638] [10.1021/acs.jmedchem.2c00203]

Source

Source(1):

• Scientific Literature