ID: ALA2335418

Max Phase: Preclinical

Molecular Formula: C21H21N5O

Molecular Weight: 359.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(-c2ccncc2)cc(C(C)C#Cc2c(C)nc(N)nc2N)c1

Standard InChI:  InChI=1S/C21H21N5O/c1-13(4-5-19-14(2)25-21(23)26-20(19)22)16-10-17(12-18(11-16)27-3)15-6-8-24-9-7-15/h6-13H,1-3H3,(H4,22,23,25,26)

Standard InChI Key:  ULSWBNKDTMSHNY-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: 359.43

Molecular Weight (Monoisotopic): 359.1746

AlogP: 3.18

#Rotatable Bonds: 3

Polar Surface Area: 99.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.29

CX LogP: 2.92

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.56

References

1. 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]

2. Zhou W, Viswanathan K, Hill D, Anderson AC, Wright DL..  (2012)  Acetylenic linkers in lead compounds: a study of the stability of the propargyl-linked antifolates.,  40  (10): [PMID:22815313] [10.1124/dmd.112.046870]

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

Source

Source(2):

• Scientific Literature
• BindingDB Database