ID: ALA3827532

Max Phase: Preclinical

Molecular Formula: C23H22N4O3

Molecular Weight: 402.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCc1nc(N)nc(N)c1C#CCc1cc(-c2ccc(C(=O)O)cc2)ccc1OC

Standard InChI:  InChI=1S/C23H22N4O3/c1-3-19-18(21(24)27-23(25)26-19)6-4-5-17-13-16(11-12-20(17)30-2)14-7-9-15(10-8-14)22(28)29/h7-13H,3,5H2,1-2H3,(H,28,29)(H4,24,25,26,27)

Standard InChI Key:  KQGRJTMRAQWNLV-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: 402.45

Molecular Weight (Monoisotopic): 402.1692

AlogP: 3.17

#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: 3.08

CX Basic pKa: 8.12

CX LogP: 2.04

CX LogD: 1.98

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: -0.29

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]

Source

Source(1):

• Scientific Literature