ID: ALA1270837

Max Phase: Preclinical

Molecular Formula: C22H22N4O

Molecular Weight: 358.45

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  COc1cc(-c2ccccc2)ccc1C(C)C#Cc1c(C)nc(N)nc1N

Standard InChI:  InChI=1S/C22H22N4O/c1-14(9-11-19-15(2)25-22(24)26-21(19)23)18-12-10-17(13-20(18)27-3)16-7-5-4-6-8-16/h4-8,10,12-14H,1-3H3,(H4,23,24,25,26)

Standard InChI Key:  DATCFVVEPPDLRQ-UHFFFAOYSA-N

Associated Targets(Human)

Dihydrofolate reductase 3072 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

MCF10 107 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Dihydrofolate reductase 135 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Dihydrofolate reductase 308 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Nakaseomyces glabratus 9108 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Candida albicans 78123 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Bifunctional dihydrofolate reductase-thymidylate synthase 52 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: 358.45Molecular Weight (Monoisotopic): 358.1794AlogP: 3.78#Rotatable Bonds: 3
Polar Surface Area: 87.05Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: 0HBA (Lipinski): 5HBD (Lipinski): 4#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: 7.29CX LogP: 4.14CX LogD: 3.89
Aromatic Rings: 3Heavy Atoms: 27QED Weighted: 0.70Np Likeness Score: -0.38

References

1. 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]
2. 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]
3.  (2014)  Heterocyclic analogs of propargyl-linked inhibitors of dihydrofolate reductase,