ID: ALA440562

Max Phase: Preclinical

Molecular Formula: C11H8N2O4

Molecular Weight: 232.19

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)c1nc(-c2ccccc2)nc(O)c1O

Standard InChI:  InChI=1S/C11H8N2O4/c14-8-7(11(16)17)12-9(13-10(8)15)6-4-2-1-3-5-6/h1-5,14H,(H,16,17)(H,12,13,15)

Standard InChI Key:  ZCILTNACHNCSCB-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: 232.19

Molecular Weight (Monoisotopic): 232.0484

AlogP: 1.25

#Rotatable Bonds: 2

Polar Surface Area: 103.54

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.05

CX Basic pKa: 16.02

CX LogP: 0.70

CX LogD: -0.62

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.72

Np Likeness Score: -0.84

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. Summa V, Petrocchi A, Matassa VG, Taliani M, Laufer R, De Francesco R, Altamura S, Pace P..  (2004)  HCV NS5b RNA-dependent RNA polymerase inhibitors: from alpha,gamma-diketoacids to 4,5-dihydroxypyrimidine- or 3-methyl-5-hydroxypyrimidinonecarboxylic acids. Design and synthesis.,  47  (22): [PMID:15481971] [10.1021/jm0494669]

3. 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]

4. Kirschberg TA, Balakrishnan M, Squires NH, Barnes T, Brendza KM, Chen X, Eisenberg EJ, Jin W, Kutty N, Leavitt S, Liclican A, Liu Q, Liu X, Mak J, Perry JK, Wang M, Watkins WJ, Lansdon EB..  (2009)  RNase H active site inhibitors of human immunodeficiency virus type 1 reverse transcriptase: design, biochemical activity, and structural information.,  52  (19): [PMID:19791799] [10.1021/jm900597q]

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