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Compounds
ALA584391

(+/-)-5-(3-(5-methoxy-4'-methylbiphenyl-3-yl)but-1-ynyl)-6-methylpyrimidine-2,4-diamine

ID: ALA584391

Chembl Id: CHEMBL584391

PubChem CID: 25195125

Max Phase: Preclinical

Molecular Formula: C23H24N4O

Molecular Weight: 372.47

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: COc1cc(-c2ccc(C)cc2)cc(C(C)C#Cc2c(C)nc(N)nc2N)c1

Standard InChI: InChI=1S/C23H24N4O/c1-14-5-8-17(9-6-14)19-11-18(12-20(13-19)28-4)15(2)7-10-21-16(3)26-23(25)27-22(21)24/h5-6,8-9,11-13,15H,1-4H3,(H4,24,25,26,27)

Standard InChI Key: QVXYJVHNRPNRJL-UHFFFAOYSA-N

Alternative Forms

Parent:

ALA584391
5-[3-[3-Methoxy-5-(p-tolyl)phenyl]but-1-ynyl]-6-methyl-pyrimidine-2,4-diamine

Associated Targets(Human)

DHFR Tclin Dihydrofolate reductase (3072 Activities)

Discover Target: DHFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

DFR1 Dihydrofolate reductase (308 Activities)

Discover Target: DFR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Candida albicans (78123 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nakaseomyces glabratus (9108 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

folA Dihydrofolate reductase (367 Activities)

Discover Target: folA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Dihydrofolate reductase (15 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 372.47	Molecular Weight (Monoisotopic): 372.1950	AlogP: 4.09	#Rotatable Bonds: 3
Polar Surface Area: 87.05	Molecular Species: NEUTRAL	HBA: 5	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 5	HBD (Lipinski): 4	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: ┄	CX Basic pKa: 7.29	CX LogP: 4.65	CX LogD: 4.41
Aromatic Rings: 3	Heavy Atoms: 28	QED Weighted: 0.68	Np Likeness Score: -0.54

References

1. 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]
2. 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]
3. Zhou W, Scocchera EW, Wright DL, Anderson AC. (2013) Antifolates as effective antimicrobial agents: new generations of trimethoprim analogs, 4 (6): [10.1039/C3MD00104K]
4. (2014) Heterocyclic analogs of propargyl-linked inhibitors of dihydrofolate reductase,

Source

Source(2):