ID: ALA3828581

Max Phase: Preclinical

Molecular Formula: C24H24N4O3

Molecular Weight: 416.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCc1nc(N)nc(N)c1C#C[C@@H](C)c1cc(OC)cc(-c2ccc(C(=O)O)cc2)c1

Standard InChI:  InChI=1S/C24H24N4O3/c1-4-21-20(22(25)28-24(26)27-21)10-5-14(2)17-11-18(13-19(12-17)31-3)15-6-8-16(9-7-15)23(29)30/h6-9,11-14H,4H2,1-3H3,(H,29,30)(H4,25,26,27,28)/t14-/m1/s1

Standard InChI Key:  OKJCHFXBCVXSIZ-CQSZACIVSA-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: 416.48

Molecular Weight (Monoisotopic): 416.1848

AlogP: 3.73

#Rotatable Bonds: 5

Polar Surface Area: 124.35

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.06

CX Basic pKa: 8.12

CX LogP: 2.33

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -0.41

References

1. Scocchera E, Reeve SM, Keshipeddy S, Lombardo MN, Hajian B, Sochia AE, Alverson JB, Priestley ND, Anderson AC, Wright DL..  (2016)  Charged Nonclassical Antifolates with Activity Against Gram-Positive and Gram-Negative Pathogens.,  7  (7): [PMID:27437079] [10.1021/acsmedchemlett.6b00120]

2. Reeve SM, Scocchera E, Ferreira JJ, G-Dayanandan N, Keshipeddy S, Wright DL, Anderson AC..  (2016)  Charged Propargyl-Linked Antifolates Reveal Mechanisms of Antifolate Resistance and Inhibit Trimethoprim-Resistant MRSA Strains Possessing Clinically Relevant Mutations.,  59  (13): [PMID:27308944] [10.1021/acs.jmedchem.6b00688]

3. He J, Qiao W, An Q, Yang T, Luo Y..  (2020)  Dihydrofolate reductase inhibitors for use as antimicrobial agents.,  195  [PMID:32298876] [10.1016/j.ejmech.2020.112268]

Source

Source(1):

• Scientific Literature