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ID: ALA1096834
Max Phase: Preclinical
Molecular Formula: C18H21N3O
Molecular Weight: 295.39
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(NCc2ccccc2)c2ncn(C(C)C)c2c1
Standard InChI: InChI=1S/C18H21N3O/c1-13(2)21-12-20-18-16(9-15(22-3)10-17(18)21)19-11-14-7-5-4-6-8-14/h4-10,12-13,19H,11H2,1-3H3
Standard InChI Key: XNTDNBYHJFCUMA-UHFFFAOYSA-N
Associated Targets(Human)
Dual specificity mitogen-activated protein kinase kinase 5 650 Activities
CCRF-CEM 65223 Activities
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HL-60(TB) 4309 Activities
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K562 73714 Activities
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MOLT-4 49676 Activities
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SR 39847 Activities
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A549 127892 Activities
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EKVX 44102 Activities
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HOP-62 47048 Activities
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HOP-92 41141 Activities
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NCI-H226 44470 Activities
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NCI-H23 49055 Activities
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NCI-H322M 45589 Activities
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NCI-H460 60772 Activities
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NCI-H522 44358 Activities
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COLO 205 50209 Activities
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HCC 2998 41480 Activities
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HCT-116 91556 Activities
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HCT-15 51914 Activities
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HT-29 80576 Activities
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KM12 47707 Activities
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SW-620 52400 Activities
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SF-268 49410 Activities
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SF-295 48000 Activities
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SF-539 44845 Activities
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SNB-19 46794 Activities
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SNB-75 44215 Activities
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U-251 51189 Activities
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LOX IMVI 44321 Activities
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Malme-3M 44254 Activities
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M14 47487 Activities
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MDA-MB-435 38290 Activities
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SK-MEL-2 46422 Activities
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SK-MEL-28 48833 Activities
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SK-MEL-5 47095 Activities
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UACC-257 46019 Activities
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UACC-62 47335 Activities
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IGROV-1 47897 Activities
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OVCAR-3 48710 Activities
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OVCAR-4 44535 Activities
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OVCAR-5 45555 Activities
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OVCAR-8 47708 Activities
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SK-OV-3 52876 Activities
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786-0 47912 Activities
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A498 42825 Activities
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ACHN 49357 Activities
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CAKI-1 44928 Activities
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RXF 393 41971 Activities
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SN12C 47755 Activities
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TK-10 45540 Activities
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UO-31 46270 Activities
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DU-145 51482 Activities
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MCF7 126967 Activities
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MDA-MB-231 73002 Activities
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BT-549 31254 Activities
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T47D 39041 Activities
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MDA-MB-468 9477 Activities
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NCI/ADR-RES 33767 Activities
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Dual specificity mitogen-activated protein kinase kinase; MEK1/2 426 Activities
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Cyclin-dependent kinase 5/CDK5 activator 1 3697 Activities
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Lysine-specific demethylase 4A 52245 Activities
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Bromodomain adjacent to zinc finger domain protein 2B 56204 Activities
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Glucose-6-phosphate 1-dehydrogenase 778 Activities
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DNA polymerase iota 116820 Activities
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Isocitrate dehydrogenase [NADP] cytoplasmic 40980 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Geminin 128009 Activities
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Glucagon-like peptide 1 receptor 111429 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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Ubiquitin carboxyl-terminal hydrolase 1 22556 Activities
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Associated Targets(non-human)
Saccharomyces cerevisiae 19171 Activities
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Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase 1761 Activities
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Plasmodium falciparum 966862 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 |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 295.39 | Molecular Weight (Monoisotopic): 295.1685 | AlogP: 4.24 | #Rotatable Bonds: 5 |
| Polar Surface Area: 39.08 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 6.21 | CX LogP: 3.30 | CX LogD: 3.27 |
| Aromatic Rings: 3 | Heavy Atoms: 22 | QED Weighted: 0.76 | Np Likeness Score: -0.96 |
References
| 1. Flaherty PT, Chopra I, Jain P, Yi S, Allen E, Cavanaugh J.. (2010) Identification of benzimidazole-based inhibitors of the mitogen activated kinase-5 signaling pathway., 20 (9): [PMID:20382528] [10.1016/j.bmcl.2010.03.033] |
| 2. Flaherty PT, Chopra I, Jain P, Monlish D, Cavanaugh J.. (2010) Structure-activity relationships of benzimidazole-based selective inhibitors of the mitogen activated kinase-5 signaling pathway., 18 (22): [PMID:20965737] [10.1016/j.bmc.2010.09.017] |
| 3. PubChem BioAssay data set, |
| 4. Jain P, Flaherty PT, Yi S, Chopra I, Bleasdell G, Lipay J, Ferandin Y, Meijer L, Madura JD.. (2011) Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25., 19 (1): [PMID:21144757] [10.1016/j.bmc.2010.11.022] |
Source
Source(2):