N-(4-fluorobenzyl)-5,6-dihydroxy-2-methylpyrimidine-4-carboxamide

ID: ALA217285

Chembl Id: CHEMBL217285

PubChem CID: 135602046

Max Phase: Preclinical

Molecular Formula: C13H12FN3O3

Molecular Weight: 277.25

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1nc(C(=O)NCc2ccc(F)cc2)c(O)c(=O)[nH]1

Standard InChI:  InChI=1S/C13H12FN3O3/c1-7-16-10(11(18)13(20)17-7)12(19)15-6-8-2-4-9(14)5-3-8/h2-5,18H,6H2,1H3,(H,15,19)(H,16,17,20)

Standard InChI Key:  QUOVSBFFBCDNHK-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA217285

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Associated Targets(Human)

MMP12 Tchem Matrix metalloproteinase 12 (1130 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRSS1 Tclin Trypsin (2137 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC2 Tclin Histone deacetylase 2 (3971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Human immunodeficiency virus (3636 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pol Human immunodeficiency virus type 1 integrase (9041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPO2 Tyrosinase (3884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TRM3 Tripartite terminase subunit 3 (246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 277.25Molecular Weight (Monoisotopic): 277.0863AlogP: 0.85#Rotatable Bonds: 3
Polar Surface Area: 95.08Molecular Species: NEUTRALHBA: 4HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 7.24CX Basic pKa: CX LogP: 0.16CX LogD: -0.24
Aromatic Rings: 2Heavy Atoms: 20QED Weighted: 0.77Np Likeness Score: -1.44

References

1. Summa V, Petrocchi A, Matassa VG, Gardelli C, Muraglia E, Rowley M, Paz OG, Laufer R, Monteagudo E, Pace P..  (2006)  4,5-dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species.,  49  (23): [PMID:17154493] [10.1021/jm060854f]
2. Pace P, Di Francesco ME, Gardelli C, Harper S, Muraglia E, Nizi E, Orvieto F, Petrocchi A, Poma M, Rowley M, Scarpelli R, Laufer R, Gonzalez Paz O, Monteagudo E, Bonelli F, Hazuda D, Stillmock KA, Summa V..  (2007)  Dihydroxypyrimidine-4-carboxamides as novel potent and selective HIV integrase inhibitors.,  50  (9): [PMID:17428043] [10.1021/jm070027u]
3. Tang J, Maddali K, Pommier Y, Sham YY, Wang Z..  (2010)  Scaffold rearrangement of dihydroxypyrimidine inhibitors of HIV integrase: Docking model revisited.,  20  (11): [PMID:20457521] [10.1016/j.bmcl.2010.04.048]
4. Day JA, Cohen SM..  (2013)  Investigating the selectivity of metalloenzyme inhibitors.,  56  (20): [PMID:24074025] [10.1021/jm401053m]
5. 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