ID: ALA181653

Max Phase: Preclinical

Molecular Formula: C9H6N2O4S

Molecular Weight: 238.22

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C9H6N2O4S/c12-6-5(9(14)15)10-7(11-8(6)13)4-2-1-3-16-4/h1-3,12H,(H,14,15)(H,10,11,13)

Standard InChI Key:  SSOGKSFNCMYOPA-UHFFFAOYSA-N

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

Properties

Molecular Weight: 238.22

Molecular Weight (Monoisotopic): 238.0048

AlogP: 1.31

#Rotatable Bonds: 2

Polar Surface Area: 103.54

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.03

CX Basic pKa: 15.64

CX LogP: 0.47

CX LogD: -0.98

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.73

Np Likeness Score: -1.47

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. Petrocchi A, Koch U, Matassa VG, Pacini B, Stillmock KA, Summa V..  (2007)  From dihydroxypyrimidine carboxylic acids to carboxamide HIV-1 integrase inhibitors: SAR around the amide moiety.,  17  (2): [PMID:17107799] [10.1016/j.bmcl.2006.10.054]

4. Iannazzo D, Piperno A, Romeo G, Romeo R, Chiacchio U, Rescifina A, Balestrieri E, Macchi B, Mastino A, Cortese R..  (2008)  3-Amino-2(5H)furanones as inhibitors of subgenomic hepatitis C virus RNA replication.,  16  (21): [PMID:18835180] [10.1016/j.bmc.2008.09.006]

5. 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]

6. 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]

7. Lacbay CM, Menni M, Bernatchez JA, Götte M, Tsantrizos YS..  (2018)  Pharmacophore requirements for HIV-1 reverse transcriptase inhibitors that selectively "Freeze" the pre-translocated complex during the polymerization catalytic cycle.,  26  (8): [PMID:29478802] [10.1016/j.bmc.2018.02.017]

8. 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