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ID: ALA1834323
Max Phase: Preclinical
Molecular Formula: C20H20FN5O4
Molecular Weight: 413.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: C[C@H]1COc2c(NCCNc3ccccn3)c(F)c(N)c3c(=O)c(C(=O)O)cn1c23
Standard InChI: InChI=1S/C20H20FN5O4/c1-10-9-30-19-16(25-7-6-24-12-4-2-3-5-23-12)14(21)15(22)13-17(19)26(10)8-11(18(13)27)20(28)29/h2-5,8,10,25H,6-7,9,22H2,1H3,(H,23,24)(H,28,29)/t10-/m0/s1
Standard InChI Key: BEOOHAUYYYZCER-JTQLQIEISA-N
Associated Targets(Human)
Glycogen synthase kinase-3 beta 11785 Activities
Glycogen synthase kinase-3 alpha 3764 Activities
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Tyrosine-protein kinase ABL 162 Activities
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AMP-activated protein kinase, AMPK 12273 Activities
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Cyclin-dependent kinase 10 88 Activities
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Cyclin-dependent kinase 2 9050 Activities
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Cyclin-dependent kinase 5 3021 Activities
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Cyclin-dependent kinase 6 1724 Activities
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Cyclin-dependent kinase 7 1512 Activities
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Cyclin-dependent kinase 9 2495 Activities
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Cyclin-dependent kinase 13 570 Activities
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Dual specificity tyrosine-phosphorylation-regulated kinase 1B 2654 Activities
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Mitogen-activated protein kinase; ERK1/ERK2 651 Activities
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c-Jun N-terminal kinase 1 5038 Activities
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Serine/threonine-protein kinase 11 1020 Activities
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MAP kinase p38 alpha 12866 Activities
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MAP kinase p38 delta 2605 Activities
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p38 delta/gamma 17 Activities
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DNA-dependent protein kinase 1929 Activities
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Serine/threonine-protein kinase ULK3 913 Activities
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c-Jun N-terminal kinase 2 4655 Activities
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c-Jun N-terminal kinase 3 3396 Activities
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Serine/threonine-protein kinase AKT 9192 Activities
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Serine/threonine-protein kinase AKT2 4301 Activities
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Myotonin-protein kinase 927 Activities
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Ribosomal protein S6 kinase alpha 5 3355 Activities
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cAMP-dependent protein kinase alpha-catalytic subunit 3475 Activities
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cAMP-dependent protein kinase, gamma catalytic subunit 229 Activities
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Protein kinase C alpha 5923 Activities
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Protein kinase C beta 4071 Activities
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Protein kinase N2 1991 Activities
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Rho-associated protein kinase 1 4723 Activities
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Rho-associated protein kinase 2 6206 Activities
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Ribosomal protein S6 kinase delta-1 23 Activities
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Serine/threonine-protein kinase Sgk3 1431 Activities
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Serine/threonine-protein kinase EEF2K 1246 Activities
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CaM kinase II gamma 1752 Activities
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Serine/threonine-protein kinase Chk1 6846 Activities
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Serine/threonine-protein kinase DCLK1 1025 Activities
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Serine/threonine-protein kinase c-TAK1 2532 Activities
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Phosphorylase kinase gamma subunit 2 2281 Activities
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Protein kinase C mu 1904 Activities
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Serine/threonine-protein kinase D2 2847 Activities
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Ribosomal protein S6 kinase alpha 1 2796 Activities
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Ribosomal protein S6 kinase alpha 3 4284 Activities
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Ribosomal protein S6 kinase alpha 2 2184 Activities
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Ribosomal protein S6 kinase alpha 6 2027 Activities
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Casein kinase I alpha 2581 Activities
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Serine/threonine-protein kinase mTOR 13850 Activities
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PI4-kinase alpha subunit 184 Activities
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Phosphatidylinositol-5-phosphate 4-kinase type-2 alpha 1501 Activities
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Serine/threonine-protein kinase SMG1 61 Activities
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Serine/threonine-protein kinase Aurora-A 10240 Activities
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Serine/threonine-protein kinase Aurora-B 6805 Activities
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Serine/threonine-protein kinase Aurora-C 1780 Activities
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Inhibitor of nuclear factor kappa B kinase alpha subunit 3170 Activities
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Inhibitor of nuclear factor kappa B kinase beta subunit 5554 Activities
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Serine/threonine-protein kinase/endoribonuclease IRE1 1682 Activities
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Serine/threonine-protein kinase 16 910 Activities
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Serine/threonine-protein kinase NEK6 1986 Activities
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Serine/threonine-protein kinase NEK7 1804 Activities
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Serine/threonine-protein kinase NEK9 1479 Activities
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Eukaryotic translation initiation factor 2-alpha kinase 3 635 Activities
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Interferon-induced, double-stranded RNA-activated protein kinase 504 Activities
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Serine/threonine-protein kinase PLK1 28605 Activities
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Serine/threonine-protein kinase WEE1 1772 Activities
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Serine/threonine-protein kinase WNK1 297 Activities
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Serine/threonine-protein kinase WNK2 570 Activities
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Serine/threonine-protein kinase WNK4 156 Activities
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Heat-stable enterotoxin receptor 5 Activities
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Mitogen-activated protein kinase kinase kinase kinase 1 947 Activities
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Mitogen-activated protein kinase kinase kinase kinase 5 1523 Activities
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Mitogen-activated protein kinase kinase kinase kinase 3 674 Activities
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Serine/threonine-protein kinase 10 2119 Activities
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Dual specificity mitogen-activated protein kinase kinase 1 4127 Activities
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Dual specificity mitogen-activated protein kinase kinase 4 1051 Activities
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Mitogen-activated protein kinase kinase kinase 2 593 Activities
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Mitogen-activated protein kinase kinase kinase 5 1965 Activities
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Serine/threonine-protein kinase MST1 2643 Activities
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Serine/threonine-protein kinase MST2 3069 Activities
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Serine/threonine-protein kinase MST4 1915 Activities
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Serine/threonine-protein kinase 25 577 Activities
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Serine/threonine-protein kinase OSR1 463 Activities
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Tyrosine-protein kinase FYN 5308 Activities
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STE20-related kinase adapter protein alpha 270 Activities
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Serine/threonine-protein kinase TAO1 2019 Activities
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Serine/threonine-protein kinase TAO2 964 Activities
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Serine/threonine-protein kinase TAO3 1005 Activities
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Tyrosine-protein kinase CSK 2395 Activities
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Tyrosine-protein kinase FER 2362 Activities
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Tyrosine-protein kinase FES 2339 Activities
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Tyrosine-protein kinase FGR 1748 Activities
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Tyrosine-protein kinase JAK1 8569 Activities
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Tyrosine-protein kinase Lyn 4251 Activities
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Protein tyrosine kinase 2 beta 2827 Activities
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Tyrosine-protein kinase SYK 7372 Activities
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Serine/threonine-protein kinase A-Raf 405 Activities
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Serine/threonine-protein kinase B-raf 11587 Activities
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Interleukin-1 receptor-associated kinase 4 5917 Activities
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Receptor-interacting serine/threonine-protein kinase 3 468 Activities
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Nuclear receptor subfamily 2 group C member 2 42 Activities
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Mixed lineage kinase 7 1473 Activities
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Associated Targets(non-human)
Escherichia coli 133304 Activities
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Staphylococcus aureus 210822 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: 413.41 | Molecular Weight (Monoisotopic): 413.1499 | AlogP: 2.29 | #Rotatable Bonds: 6 |
| Polar Surface Area: 131.50 | Molecular Species: ACID | HBA: 8 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 9 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 5.70 | CX Basic pKa: 6.68 | CX LogP: 0.49 | CX LogD: -0.11 |
| Aromatic Rings: 3 | Heavy Atoms: 30 | QED Weighted: 0.36 | Np Likeness Score: -0.51 |
References
| 1. Cociorva OM, Li B, Nomanbhoy T, Li Q, Nakamura A, Nakamura K, Nomura M, Okada K, Seto S, Yumoto K, Liyanage M, Zhang MC, Aban A, Leen B, Szardenings AK, Rosenblum JS, Kozarich JW, Kohno Y, Shreder KR.. (2011) Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β., 21 (19): [PMID:21873061] [10.1016/j.bmcl.2011.07.073] |
| 2. Li B, Cociorva OM, Nomanbhoy T, Li Q, Nakamura K, Nomura M, Okada K, Yumoto K, Liyanage M, Zhang MC, Aban A, Szardenings AK, Kozarich JW, Kohno Y, Shreder KR.. (2012) 6-Position optimization of tricyclic 4-quinolone-based inhibitors of glycogen synthase kinase-3β: discovery of nitrile derivatives with picomolar potency., 22 (2): [PMID:22202172] [10.1016/j.bmcl.2011.12.006] |
Source
Source(1):