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Methyl4-[(5-[(2,4-diamino-6-quinazolinyl)methyl]amino-2-methoxyphenoxy)methyl]benzene carboxylate ID: ALA1165306
PubChem CID: 46907163
Max Phase: Preclinical
Molecular Formula: C25H25N5O4
Molecular Weight: 459.51
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: COC(=O)c1ccc(COc2cc(NCc3ccc4nc(N)nc(N)c4c3)ccc2OC)cc1
Standard InChI: InChI=1S/C25H25N5O4/c1-32-21-10-8-18(12-22(21)34-14-15-3-6-17(7-4-15)24(31)33-2)28-13-16-5-9-20-19(11-16)23(26)30-25(27)29-20/h3-12,28H,13-14H2,1-2H3,(H4,26,27,29,30)
Standard InChI Key: BYCSTMIHRAHFHA-UHFFFAOYSA-N
Molfile:
RDKit 2D
34 37 0 0 0 0 0 0 0 0999 V2000
12.3497 -5.7819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.0662 -5.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.0633 -4.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.3479 -4.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.6349 -5.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.6372 -4.5434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.9245 -4.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.2091 -4.5419 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
10.2108 -5.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.9240 -5.7799 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
13.7762 -4.1228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.4922 -4.5326 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
15.2052 -4.1174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.9196 -4.5307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.6320 -4.1162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.6293 -3.2903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.9083 -2.8807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.1988 -3.2975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.3478 -4.5263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
17.3417 -2.8741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
10.9259 -3.3055 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
9.4973 -5.7848 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
18.0609 -4.1115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.7768 -4.5216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.7859 -5.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.4973 -5.7544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.2099 -5.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.2077 -4.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.4868 -4.1044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.0583 -3.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.9256 -5.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.9279 -6.5758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
21.6389 -5.3363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
22.3545 -5.7468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7 8 1 0
16 17 1 0
3 4 2 0
17 18 2 0
18 13 1 0
8 9 2 0
15 19 1 0
4 6 1 0
16 20 1 0
9 10 1 0
7 21 1 0
10 5 2 0
9 22 1 0
1 2 2 0
19 23 1 0
3 11 1 0
23 24 1 0
5 1 1 0
11 12 1 0
25 26 2 0
5 6 1 0
26 27 1 0
12 13 1 0
27 28 2 0
2 3 1 0
28 29 1 0
29 24 2 0
24 25 1 0
13 14 2 0
20 30 1 0
6 7 2 0
27 31 1 0
14 15 1 0
31 32 2 0
31 33 1 0
15 16 2 0
33 34 1 0
M END Associated Targets(Human) Associated Targets(non-human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 459.51Molecular Weight (Monoisotopic): 459.1907AlogP: 3.78#Rotatable Bonds: 8Polar Surface Area: 134.61Molecular Species: NEUTRALHBA: 9HBD: 3#RO5 Violations: ┄HBA (Lipinski): 9HBD (Lipinski): 5#RO5 Violations (Lipinski): ┄CX Acidic pKa: ┄CX Basic pKa: 6.99CX LogP: 3.65CX LogD: 3.51Aromatic Rings: 4Heavy Atoms: 34QED Weighted: 0.34Np Likeness Score: -0.83
References 1. Schormann N, Velu SE, Murugesan S, Senkovich O, Walker K, Chenna BC, Shinkre B, Desai A, Chattopadhyay D.. (2010) Synthesis and characterization of potent inhibitors of Trypanosoma cruzi dihydrofolate reductase., 18 (11): [PMID:20452776 ] [10.1016/j.bmc.2010.04.020 ]