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ID: ALA187631
PubChem CID: 45027828
Max Phase: Preclinical
Molecular Formula: C21H19ClN2O6
Molecular Weight: 394.38
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: COc1cc2c3c(n(CCN)c(=O)c2cc1OC)-c1cc2c(cc1C3=O)OCO2.Cl
Standard InChI: InChI=1S/C21H18N2O6.ClH/c1-26-14-5-10-13(8-15(14)27-2)21(25)23(4-3-22)19-11-6-16-17(29-9-28-16)7-12(11)20(24)18(10)19;/h5-8H,3-4,9,22H2,1-2H3;1H
Standard InChI Key: HGKJLPYOQQNYSU-UHFFFAOYSA-N
Molfile:
RDKit 2D 30 33 0 0 0 0 0 0 0 0999 V2000 4.0542 -0.0917 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.3875 -0.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6708 -1.0750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6708 -1.9000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3833 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2208 0.1583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1000 -1.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0583 -0.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0958 -1.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3958 0.2458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7667 -0.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0917 0.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8208 -0.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8208 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9167 0.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2542 0.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5333 -1.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5333 -1.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3833 -3.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7708 0.7708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0792 0.1583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5375 1.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2542 0.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0500 -2.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2458 -2.3167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2458 -0.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4792 -2.3042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7625 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2458 -3.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9708 -1.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2 0 4 3 1 0 5 9 1 0 6 2 1 0 7 2 1 0 8 3 1 0 9 7 1 0 10 6 1 0 11 8 1 0 12 10 1 0 13 7 2 0 14 9 2 0 15 12 2 0 16 11 2 0 17 18 2 0 18 13 1 0 19 5 2 0 20 6 2 0 21 16 1 0 22 15 1 0 23 22 1 0 24 4 1 0 25 17 1 0 26 18 1 0 27 28 1 0 28 24 1 0 29 25 1 0 30 26 1 0 10 8 2 0 4 5 1 0 14 17 1 0 15 16 1 0 21 23 1 0 M END
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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 |
Molecular Weight: 394.38 | Molecular Weight (Monoisotopic): 394.1165 | AlogP: 1.92 | #Rotatable Bonds: 4 |
Polar Surface Area: 102.01 | Molecular Species: BASE | HBA: 8 | HBD: 1 |
#RO5 Violations: ┄ | HBA (Lipinski): 8 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: ┄ | CX Basic pKa: 8.79 | CX LogP: 0.63 | CX LogD: -0.77 |
Aromatic Rings: 3 | Heavy Atoms: 29 | QED Weighted: 0.56 | Np Likeness Score: 0.42 |
1. Nagarajan M, Xiao X, Antony S, Kohlhagen G, Pommier Y, Cushman M.. (2003) Design, synthesis, and biological evaluation of indenoisoquinoline topoisomerase I inhibitors featuring polyamine side chains on the lactam nitrogen., 46 (26): [PMID:14667224] [10.1021/jm030313f] |
2. Nagarajan M, Morrell A, Fort BC, Meckley MR, Antony S, Kohlhagen G, Pommier Y, Cushman M.. (2004) Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings., 47 (23): [PMID:15509164] [10.1021/jm040025z] |
3. Morrell A, Jayaraman M, Nagarajan M, Fox BM, Meckley MR, Ioanoviciu A, Pommier Y, Antony S, Hollingshead M, Cushman M.. (2006) Evaluation of indenoisoquinoline topoisomerase I inhibitors using a hollow fiber assay., 16 (16): [PMID:16750365] [10.1016/j.bmcl.2006.05.048] |
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