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ID: ALA60020
Max Phase: Preclinical
Molecular Formula: C11H14O3
Molecular Weight: 194.23
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: C/C=C/C(=O)OCC1=CCCCC1=O
Standard InChI: InChI=1S/C11H14O3/c1-2-5-11(13)14-8-9-6-3-4-7-10(9)12/h2,5-6H,3-4,7-8H2,1H3/b5-2+
Standard InChI Key: IQAJMALOOLNRLN-GORDUTHDSA-N
Associated Targets(Human)
HT-29 (80576 Activities)
GSTP1 Tchem Glutathione S-transferase Pi (449 Activities)
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A549 (127892 Activities)
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NCI-H460 (60772 Activities)
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GSTA4 Tbio Glutathione S-transferase A4 (4 Activities)
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GSTM2 Tchem Glutathione S-transferase Mu 2 (77 Activities)
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HepG2 (196354 Activities)
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Associated Targets(non-human)
B16 (5829 Activities)
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 194.23 | Molecular Weight (Monoisotopic): 194.0943 | AlogP: 1.79 | #Rotatable Bonds: 3 |
| Polar Surface Area: 43.37 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 2.42 | CX LogD: 2.42 |
| Aromatic Rings: 0 | Heavy Atoms: 14 | QED Weighted: 0.51 | Np Likeness Score: 1.21 |
References
| 1. Joseph E, Eiseman JL, Hamilton DS, Wang H, Tak H, Ding Z, Ganem B, Creighton DJ.. (2003) Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones., 46 (1): [PMID:12502374] [10.1021/jm0203027] |
| 2. Joseph E, Ganem B, Eiseman JL, Creighton DJ.. (2005) Selective inhibition of MCF-7(piGST) breast tumors using glutathione transferase-derived 2-methylene-cycloalkenones., 48 (21): [PMID:16220971] [10.1021/jm058245f] |
| 3. Arthurs CL, Wind NS, Whitehead RC, Stratford IJ.. (2007) Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties., 17 (2): [PMID:17174551] [10.1016/j.bmcl.2006.09.072] |
| 4. Arthurs CL, Raftery J, Whitby HL, Whitehead RC, Wind NS, Stratford IJ.. (2007) Arene cis-dihydrodiols: useful precursors for the preparation of analogues of the anti-tumour agent, 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC)., 17 (21): [PMID:17870533] [10.1016/j.bmcl.2007.07.070] |
| 5. (2008) Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, |
| 6. Liu J, Liu X, Qian J, Meng C, Zhu P, Hang J, Wang Y, Xiong B, Qiu X, Zhu W, Yang Y, Zhang Y, Ling Y.. (2020) Development of pH/Glutathione-Responsive Theranostic Agents Activated by Glutathione S-Transferase π for Human Colon Cancer., 63 (17): [PMID:32787089] [10.1021/acs.jmedchem.0c00354] |
Source
Source(1):