Standard InChI: InChI=1S/C18H14N4OS/c19-17-15-10-14(7-8-16(15)21-18(20)22-17)24(23)13-6-5-11-3-1-2-4-12(11)9-13/h1-10H,(H4,19,20,21,22)
Standard InChI Key: QSWGIUCUSOBPPC-UHFFFAOYSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
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Associated Targets(non-human)
Dihydrofolate reductase 2343 Activities
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Plasmodium berghei 192651 Activities
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Plasmodium gallinaceum 527 Activities
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Plasmodium falciparum 966862 Activities
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Enterococcus faecalis 29875 Activities
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Staphylococcus aureus 210822 Activities
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Pseudomonas aeruginosa 123386 Activities
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Escherichia coli 133304 Activities
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Shigella sonnei 625 Activities
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Mycobacterium tuberculosis 203094 Activities
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Dihydrofolate reductase 93 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: 334.40
Molecular Weight (Monoisotopic): 334.0888
AlogP: 3.11
#Rotatable Bonds: 2
Polar Surface Area: 100.88
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: 6.77
CX LogP: 2.84
CX LogD: 2.75
Aromatic Rings: 4
Heavy Atoms: 24
QED Weighted: 0.55
Np Likeness Score: -0.42
References
1.Ghose AK, Crippen GM.. (1983) Combined distance geometry analysis of dihydrofolate reductase inhibition by quinazolines and triazines., 26 (7):[PMID:6864738][10.1021/jm00361a012]
2.Crippen GM.. (1980) Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors., 23 (6):[PMID:7392027][10.1021/jm00180a004]
3.Battershell C, Malhotra D, Hopfinger AJ.. (1981) Inhibition of dihydrofolate reductase: structure-activity correlations of quinazolines based upon molecular shape analysis., 24 (7):[PMID:7277385][10.1021/jm00139a009]
4.Ghose AK, Crippen GM.. (1982) Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors., 25 (8):[PMID:7120278][10.1021/jm00350a003]
5.Ghose AK, Crippen GM.. (1984) General distance geometry three-dimensional receptor model for diverse dihydrofolate reductase inhibitors., 27 (7):[PMID:6737433][10.1021/jm00373a016]
6.Elslager EF, Hutt MP, Jacob P, Johnson J, Temporelli B, Werbel LM, Worth DF, Rane L.. (1979) Folate antagonists. 15. 2,3-Diamino-6-(2-naphthylsulfonyl)quinazoline and related 2,4-diamino-6-[(phenyl and naphthyl)sulfinyl and sulfonyl]quinazolines, a potent new class of antimetabolites with phenomenal antimalarial activity., 22 (10):[PMID:117107][10.1021/jm00196a019]
7.Fukunaga JY, Hansch C, Steller EE.. (1976) Inhibition of dihydrofolate reductase. Structure-activity correlations of quinazolines., 19 (5):[PMID:1271401][10.1021/jm00227a006]
8.Hansch C, Fukunaga JY, Jow PY.. (1977) Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines., 20 (1):[PMID:319234][10.1021/jm00211a020]