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ID: ALA111620
Max Phase: Preclinical
Molecular Formula: C20H14ClF3N4O3
Molecular Weight: 450.80
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C1NC(=O)C(c2cn(CCCO)c3ncccc23)=C1c1ncc(C(F)(F)F)cc1Cl
Standard InChI: InChI=1S/C20H14ClF3N4O3/c21-13-7-10(20(22,23)24)8-26-16(13)15-14(18(30)27-19(15)31)12-9-28(5-2-6-29)17-11(12)3-1-4-25-17/h1,3-4,7-9,29H,2,5-6H2,(H,27,30,31)
Standard InChI Key: WFTBLYUVDBPJAV-UHFFFAOYSA-N
Associated Targets(Human)
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
PRKCB Tchem Protein kinase C beta (4071 Activities)
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PRKCA Tchem Protein kinase C alpha (5923 Activities)
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PRKCG Tchem Protein kinase C gamma (2471 Activities)
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CAMK4 Tbio CaM kinase IV (2116 Activities)
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CDK1 Tchem Cyclin-dependent kinase 1/cyclin B (899 Activities)
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CDK2 Tchem Cyclin-dependent kinase 2/cyclin A (2220 Activities)
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CCNE1 Tchem Cyclin-dependent kinase 2/cyclin E (1410 Activities)
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CCNE1 Tchem CDK3/cyclin E (347 Activities)
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CDK5 Tchem Cyclin-dependent kinase 5/CDK5 activator 1 (3697 Activities)
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CCND3 Tchem CDK6/cyclin D3 (897 Activities)
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CCNH Tbio Cyclin-dependent kinase 7/ cyclin H (714 Activities)
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CHEK1 Tchem Serine/threonine-protein kinase Chk1 (6846 Activities)
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CHEK2 Tchem Serine/threonine-protein kinase Chk2 (4015 Activities)
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CSNK1G1 Tchem Casein kinase I (67 Activities)
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CSNK2B Tbio Casein kinase II (1406 Activities)
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CSK Tchem Tyrosine-protein kinase CSK (2395 Activities)
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FES Tclin Tyrosine-protein kinase FES (2339 Activities)
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FGFR3 Tclin Fibroblast growth factor receptor 3 (7811 Activities)
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FYN Tclin Tyrosine-protein kinase FYN (5308 Activities)
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IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)
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CHUK Tchem Inhibitor of nuclear factor kappa B kinase alpha subunit (3170 Activities)
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IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)
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INSR Tclin Insulin receptor (5558 Activities)
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MAPK8 Tchem c-Jun N-terminal kinase 1 (5038 Activities)
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MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)
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MAPK10 Tchem c-Jun N-terminal kinase 3 (3396 Activities)
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LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
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MAPK3 Tchem MAP kinase ERK1 (4725 Activities)
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MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
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MAPKAPK2 Tchem MAP kinase-activated protein kinase 2 (4814 Activities)
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MAP2K1 Tclin Dual specificity mitogen-activated protein kinase kinase 1 (4127 Activities)
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MAP2K6 Tchem Dual specificity mitogen-activated protein kinase kinase 6 (1284 Activities)
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MAP2K7 Tchem Dual specificity mitogen-activated protein kinase kinase 7 (1145 Activities)
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RPS6KA5 Tchem Ribosomal protein S6 kinase alpha 5 (3355 Activities)
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RPS6KB2 Tchem Ribosomal protein S6 kinase (P70S6K) (90 Activities)
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PAK2 Tchem Serine/threonine-protein kinase PAK 2 (1925 Activities)
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PDGFRA Tclin Platelet-derived growth factor receptor alpha (5682 Activities)
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PDGFRB Tclin Platelet-derived growth factor receptor beta (5195 Activities)
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PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)
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AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)
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AKT2 Tchem Serine/threonine-protein kinase AKT2 (4301 Activities)
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PRKCE Tchem Protein kinase C epsilon (1520 Activities)
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PRKCQ Tchem Protein kinase C theta (3319 Activities)
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MAPKAPK5 Tchem MAP kinase-activated protein kinase 5 (2831 Activities)
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PKN2 Tchem Protein kinase N2 (1991 Activities)
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RAF1 Tclin Serine/threonine-protein kinase RAF (4169 Activities)
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ROCK2 Tclin Rho-associated protein kinase 2 (6206 Activities)
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RPS6KA2 Tchem Ribosomal protein S6 kinase alpha 2 (2184 Activities)
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RPS6KA3 Tchem Ribosomal protein S6 kinase alpha 3 (4284 Activities)
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MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)
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MAPK11 Tchem MAP kinase p38 beta (2785 Activities)
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MAPK12 Tchem MAP kinase p38 gamma (2776 Activities)
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MAPK13 Tchem MAP kinase p38 delta (2605 Activities)
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SGK1 Tchem Serine/threonine-protein kinase Sgk1 (2343 Activities)
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SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)
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SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)
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YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)
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ZAP70 Tchem Tyrosine-protein kinase ZAP-70 (2189 Activities)
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Associated Targets(non-human)
Blk Tyrosine-protein kinase BLK (38 Activities)
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Camk2a Ca2+/calmodulin-dependent protein kinase II (CaM kinase II) (58 Activities)
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Lyn Tyrosine-protein kinase Lyn (21 Activities)
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Mapk1 MAP kinase ERK2 (650 Activities)
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Map2k4 Dual specificity mitogen-activated protein kinase kinase 4 (99 Activities)
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Rock2 Rho-associated protein kinase 2 (125 Activities)
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Rps6ka1 Ribosomal protein S6 kinase alpha 1 (16 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 |
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Properties
| Molecular Weight: 450.80 | Molecular Weight (Monoisotopic): 450.0707 | AlogP: 3.05 | #Rotatable Bonds: 5 |
| Polar Surface Area: 97.11 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.65 | CX Basic pKa: 3.43 | CX LogP: 2.19 | CX LogD: 2.19 |
| Aromatic Rings: 3 | Heavy Atoms: 31 | QED Weighted: 0.58 | Np Likeness Score: -0.91 |
References
| 1. Zhang HC, Ye H, Conway BR, Derian CK, Addo MF, Kuo GH, Hecker LR, Croll DR, Li J, Westover L, Xu JZ, Look R, Demarest KT, Andrade-Gordon P, Damiano BP, Maryanoff BE.. (2004) 3-(7-Azaindolyl)-4-arylmaleimides as potent, selective inhibitors of glycogen synthase kinase-3., 14 (12): [PMID:15149684] [10.1016/j.bmcl.2004.03.090] |
| 2. Saraswati AP, Ali Hussaini SM, Krishna NH, Babu BN, Kamal A.. (2018) Glycogen synthase kinase-3 and its inhibitors: Potential target for various therapeutic conditions., 144 [PMID:29306837] [10.1016/j.ejmech.2017.11.103] |
| 3. Xu M, Wang SL, Zhu L, Wu PY, Dai WB, Rakesh KP.. (2019) Structure-activity relationship (SAR) studies of synthetic glycogen synthase kinase-3β inhibitors: A critical review., 164 [PMID:30616053] [10.1016/j.ejmech.2018.12.073] |
Source
Source(1):