ID: ALA584391

Max Phase: Preclinical

Molecular Formula: C23H24N4O

Molecular Weight: 372.47

Molecule Type: Small molecule

Representations

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

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

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: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

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):

• Scientific Literature
• BindingDB Database