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3-Fluoro-9-methoxy-6-(3-(piperazin-1-yl)propyl)-5H-pyrido-[3',2':4,5]cyclopenta[1,2-c]isoquinoline-5,11(6H)-dione ID: ALA4063011
PubChem CID: 137635992
Max Phase: Preclinical
Molecular Formula: C23H23FN4O3
Molecular Weight: 422.46
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: COc1cnc2c(c1)C(=O)c1c-2n(CCCN2CCNCC2)c(=O)c2cc(F)ccc12
Standard InChI: InChI=1S/C23H23FN4O3/c1-31-15-12-18-20(26-13-15)21-19(22(18)29)16-4-3-14(24)11-17(16)23(30)28(21)8-2-7-27-9-5-25-6-10-27/h3-4,11-13,25H,2,5-10H2,1H3
Standard InChI Key: IDNPTPWRYDBQMT-UHFFFAOYSA-N
Molfile:
RDKit 2D
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15.4003 -6.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.1083 -6.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.1065 -5.0060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.8151 -5.4113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.8140 -6.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.5202 -6.6410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.2320 -6.2339 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
17.5225 -4.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.2314 -5.4091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.6929 -4.1989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.1461 -3.5916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
18.5071 -4.1134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.8378 -4.8609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.6488 -4.9470 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
20.1299 -4.2864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.7943 -3.5377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.9843 -3.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.5179 -7.4582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
18.9391 -6.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.9376 -7.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.6447 -7.8707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.6433 -8.6879 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
20.2727 -2.8752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
21.0856 -2.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.9322 -9.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.9288 -9.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19.6340 -10.3196 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
20.3442 -9.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.3493 -9.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.6922 -6.6425 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 6 2 0
5 4 2 0
4 1 1 0
5 6 1 0
5 9 1 0
6 7 1 0
7 8 1 0
8 10 1 0
9 10 2 0
10 14 1 0
13 11 1 0
11 9 1 0
11 12 2 0
13 14 2 0
14 15 1 0
15 16 2 0
16 17 1 0
17 18 2 0
18 13 1 0
7 19 2 0
8 20 1 0
20 21 1 0
21 22 1 0
22 23 1 0
17 24 1 0
24 25 1 0
23 26 1 0
23 30 1 0
26 27 1 0
27 28 1 0
28 29 1 0
29 30 1 0
2 31 1 0
M END Associated Targets(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: 422.46Molecular Weight (Monoisotopic): 422.1754AlogP: 2.05#Rotatable Bonds: 5Polar Surface Area: 76.46Molecular Species: BASEHBA: 7HBD: 1#RO5 Violations: ┄HBA (Lipinski): 7HBD (Lipinski): 1#RO5 Violations (Lipinski): ┄CX Acidic pKa: ┄CX Basic pKa: 9.22CX LogP: 0.81CX LogD: -0.99Aromatic Rings: 3Heavy Atoms: 31QED Weighted: 0.53Np Likeness Score: -0.59
References 1. Elsayed MSA, Su Y, Wang P, Sethi T, Agama K, Ravji A, Redon CE, Kiselev E, Horzmann KA, Freeman JL, Pommier Y, Cushman M.. (2017) Design and Synthesis of Chlorinated and Fluorinated 7-Azaindenoisoquinolines as Potent Cytotoxic Anticancer Agents That Inhibit Topoisomerase I., 60 (13): [PMID:28657311 ] [10.1021/acs.jmedchem.6b01870 ]
