ID: ALA6979

Max Phase: Preclinical

Molecular Formula: C18H14N4OS

Molecular Weight: 334.40

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  Nc1nc(N)c2cc([S+]([O-])c3ccc4ccccc4c3)ccc2n1

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

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Dihydrofolate reductase 2343 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Plasmodium berghei 192651 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Plasmodium gallinaceum 527 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Plasmodium falciparum 966862 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Enterococcus faecalis 29875 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Staphylococcus aureus 210822 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Pseudomonas aeruginosa 123386 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Escherichia coli 133304 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Shigella sonnei 625 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mycobacterium tuberculosis 203094 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Dihydrofolate reductase 93 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

Properties

Molecular Weight: 334.40Molecular Weight (Monoisotopic): 334.0888AlogP: 3.11#Rotatable Bonds: 2
Polar Surface Area: 100.88Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: 0HBA (Lipinski): 5HBD (Lipinski): 4#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: 6.77CX LogP: 2.84CX LogD: 2.75
Aromatic Rings: 4Heavy Atoms: 24QED Weighted: 0.55Np 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]

Source