Standard InChI: InChI=1S/C22H22N4O/c1-14(9-11-18-15(2)25-22(24)26-21(18)23)17-10-12-19(20(13-17)27-3)16-7-5-4-6-8-16/h4-8,10,12-14H,1-3H3,(H4,23,24,25,26)
Standard InChI Key: YYCPXVRHQUEVAW-UHFFFAOYSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
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MCF10 107 Activities
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Associated Targets(non-human)
Dihydrofolate reductase 308 Activities
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Candida albicans 78123 Activities
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Dihydrofolate reductase 135 Activities
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Nakaseomyces glabratus 9108 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: 358.45
Molecular Weight (Monoisotopic): 358.1794
AlogP: 3.78
#Rotatable Bonds: 3
Polar Surface Area: 87.05
Molecular Species: NEUTRAL
HBA: 5
HBD: 2
#RO5 Violations: 0
HBA (Lipinski): 5
HBD (Lipinski): 4
#RO5 Violations (Lipinski): 0
CX Acidic pKa:
CX Basic pKa: 7.29
CX LogP: 4.14
CX LogD: 3.89
Aromatic Rings: 3
Heavy Atoms: 27
QED Weighted: 0.70
Np Likeness Score: -0.37
References
1.Bolstad DB, Bolstad ES, Frey KM, Wright DL, Anderson AC.. (2008) Structure-based approach to the development of potent and selective inhibitors of dihydrofolate reductase from cryptosporidium., 51 (21):[PMID:18834108][10.1021/jm8009124]
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.G-Dayanandan N, Paulsen JL, Viswanathan K, Keshipeddy S, Lombardo MN, Zhou W, Lamb KM, Sochia AE, Alverson JB, Priestley ND, Wright DL, Anderson AC.. (2014) Propargyl-linked antifolates are dual inhibitors of Candida albicans and Candida glabrata., 57 (6):[PMID:24568657][10.1021/jm401916j]
