ID: ALA279509

Max Phase: Preclinical

Molecular Formula: C20H22N4O3

Molecular Weight: 366.42

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OCc1ccccc1

Standard InChI:  InChI=1S/C20H22N4O3/c1-25-16-9-14(8-15-11-23-20(22)24-19(15)21)10-17(26-2)18(16)27-12-13-6-4-3-5-7-13/h3-7,9-11H,8,12H2,1-2H3,(H4,21,22,23,24)

Standard InChI Key:  NEBFMAAUKXSAAC-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: 366.42

Molecular Weight (Monoisotopic): 366.1692

AlogP: 2.83

#Rotatable Bonds: 7

Polar Surface Area: 105.51

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.16

CX LogP: 3.01

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -0.17

References

1. Tarnchompoo B, Sirichaiwat C, Phupong W, Intaraudom C, Sirawaraporn W, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y..  (2002)  Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.,  45  (6): [PMID:11881993] [10.1021/jm010131q]

2. Roth B, Aig E, Rauckman BS, Strelitz JZ, Phillips AP, Ferone R, Bushby SR, Sigel CW..  (1981)  2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogues of trimethoprim.,  24  (8): [PMID:7035668] [10.1021/jm00140a005]

3. Rashid U, Ahmad W, Hassan SF, Qureshi NA, Niaz B, Muhammad B, Imdad S, Sajid M..  (2016)  Design, synthesis, antibacterial activity and docking study of some new trimethoprim derivatives.,  26  (23): [PMID:28327306] [10.1016/j.bmcl.2016.10.051]

Source

Source(1):

• Scientific Literature