5-Hydroxy-1-methyl-6-oxo-2-thiophen-2-yl-1,6-dihydro-pyrimidine-4-carboxylic acid

ID: ALA366051

Chembl Id: CHEMBL366051

PubChem CID: 54727893

Max Phase: Preclinical

Molecular Formula: C10H8N2O4S

Molecular Weight: 252.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(-c2cccs2)nc(C(=O)O)c(O)c1=O

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

Standard InChI Key:  CWHZCSASLVDDDM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA366051

   5-Hydroxy-1-methyl-6-oxo-2-(2-thienyl)pyrimidine-4-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: 252.25

Molecular Weight (Monoisotopic): 252.0205

AlogP: 0.91

#Rotatable Bonds: 2

Polar Surface Area: 92.42

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.26

CX Basic pKa: ┄

CX LogP: 0.86

CX LogD: -2.93

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.83

Np Likeness Score: -1.02

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. Koch U, Attenni B, Malancona S, Colarusso S, Conte I, Di Filippo M, Harper S, Pacini B, Giomini C, Thomas S, Incitti I, Tomei L, De Francesco R, Altamura S, Matassa VG, Narjes F..  (2006)  2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as inhibitors of the hepatitis C virus NS5B polymerase: discovery, SAR, modeling, and mutagenesis.,  49  (5): [PMID:16509585] [10.1021/jm051064t]

3. Pacini B, Avolio S, Ercolani C, Koch U, Migliaccio G, Narjes F, Pacini L, Tomei L, Harper S..  (2009)  2-(3-Thienyl)-5,6-dihydroxypyrimidine-4-carboxylic acids as inhibitors of HCV NS5B RdRp.,  19  (21): [PMID:19800789] [10.1016/j.bmcl.2009.06.106]

4. 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]

Source

Source(1):

• Scientific Literature