Standard InChI: InChI=1S/C17H20N4O2/c1-4-14-13(16(18)21-17(19)20-14)7-5-6-11-10-12(22-2)8-9-15(11)23-3/h8-10H,4,6H2,1-3H3,(H4,18,19,20,21)
Standard InChI Key: NNFDQABYXZBKRK-UHFFFAOYSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
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Associated Targets(non-human)
Dihydrofolate reductase 135 Activities
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Bacillus anthracis 2936 Activities
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Dihydrofolate reductase 308 Activities
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Candida albicans 78123 Activities
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Dihydrofolate reductase 367 Activities
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Staphylococcus aureus 210822 Activities
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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
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Properties
Molecular Weight: 312.37
Molecular Weight (Monoisotopic): 312.1586
AlogP: 1.81
#Rotatable Bonds: 4
Polar Surface Area: 96.28
Molecular Species: NEUTRAL
HBA: 6
HBD: 2
#RO5 Violations: 0
HBA (Lipinski): 6
HBD (Lipinski): 4
#RO5 Violations (Lipinski): 0
CX Acidic pKa:
CX Basic pKa: 7.12
CX LogP: 2.75
CX LogD: 2.57
Aromatic Rings: 2
Heavy Atoms: 23
QED Weighted: 0.84
Np Likeness Score: -0.42
References
1.Beierlein JM, Frey KM, Bolstad DB, Pelphrey PM, Joska TM, Smith AE, Priestley ND, Wright DL, Anderson AC.. (2008) Synthetic and crystallographic studies of a new inhibitor series targeting Bacillus anthracis dihydrofolate reductase., 51 (23):[PMID:19007108][10.1021/jm800776a]
2.Paulsen JL, Liu J, Bolstad DB, Smith AE, Priestley ND, Wright DL, Anderson AC.. (2009) In vitro biological activity and structural analysis of 2,4-diamino-5-(2'-arylpropargyl)pyrimidine inhibitors of Candida albicans., 17 (14):[PMID:19560363][10.1016/j.bmc.2009.06.021]
3.Beierlein JM, Karri NG, Anderson AC.. (2010) Targeted mutations of Bacillus anthracis dihydrofolate reductase condense complex structure−activity relationships., 53 (20):[PMID:20882962][10.1021/jm100727t]
4.Paulsen JL, Viswanathan K, Wright DL, Anderson AC.. (2013) Structural analysis of the active sites of dihydrofolate reductase from two species of Candida uncovers ligand-induced conformational changes shared among species., 23 (5):[PMID:23375226][10.1016/j.bmcl.2013.01.008]
5.Zhou W, Scocchera EW, Wright DL, Anderson AC. (2013) Antifolates as effective antimicrobial agents: new generations of trimethoprim analogs, 4 (6):[10.1039/C3MD00104K]
