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ID: ALA3673434
Max Phase: Preclinical
Molecular Formula: C21H24FN3O3
Molecular Weight: 385.44
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(F)ccc1-c1ccnc(NC(=O)[C@H]2CCC[C@@H](NC(C)=O)C2)c1
Standard InChI: InChI=1S/C21H24FN3O3/c1-13(26)24-17-5-3-4-15(10-17)21(27)25-20-11-14(8-9-23-20)18-7-6-16(22)12-19(18)28-2/h6-9,11-12,15,17H,3-5,10H2,1-2H3,(H,24,26)(H,23,25,27)/t15-,17+/m0/s1
Standard InChI Key: QNWXRLPZIFMTBK-DOTOQJQBSA-N
Associated Targets(Human)
CDK1 Tchem Cyclin-dependent kinase 1 (3927 Activities)
CDK9 Tchem Cyclin-dependent kinase 9 (2495 Activities)
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CDK3 Tchem Cyclin-dependent kinase 3 (565 Activities)
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IRAK1 Tchem Interleukin-1 receptor-associated kinase 1 (1749 Activities)
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CDK6 Tclin Cyclin-dependent kinase 6 (1724 Activities)
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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
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CDK5 Tchem Cyclin-dependent kinase 5 (3021 Activities)
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CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
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GSK3A Tclin Glycogen synthase kinase-3 alpha (3764 Activities)
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CDK7 Tchem Cyclin-dependent kinase 7 (1512 Activities)
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CDK5 Tchem Cyclin-dependent kinase 5/CDK5 activator 1 (3697 Activities)
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CCNE1 Tchem CDK3/Cyclin E (905 Activities)
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CDK2 Tchem CDK2/Cyclin A1 (171 Activities)
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CDK1 Tchem Cyclin-dependent kinase 1/cyclin B1 (1887 Activities)
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CCNT1 Tchem CDK9/cyclin T1 (2643 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: 385.44 | Molecular Weight (Monoisotopic): 385.1802 | AlogP: 3.53 | #Rotatable Bonds: 5 |
| Polar Surface Area: 80.32 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 12.00 | CX Basic pKa: 3.71 | CX LogP: 2.66 | CX LogD: 2.66 |
| Aromatic Rings: 2 | Heavy Atoms: 28 | QED Weighted: 0.83 | Np Likeness Score: -1.02 |
References
| 1. (2015) Inhibitors of protein kinases, |
| 2. Sonawane YA, Taylor MA, Napoleon JV, Rana S, Contreras JI, Natarajan A.. (2016) Cyclin Dependent Kinase 9 Inhibitors for Cancer Therapy., 59 (19): [PMID:27171036] [10.1021/acs.jmedchem.6b00150] |
| 3. Barlaam B,Casella R,Cidado J,Cook C,De Savi C,Dishington A,Donald CS,Drew L,Ferguson AD,Ferguson D,Glossop S,Grebe T,Gu C,Hande S,Hawkins J,Hird AW,Holmes J,Horstick J,Jiang Y,Lamb ML,McGuire TM,Moore JE,O'Connell N,Pike A,Pike KG,Proia T,Roberts B,San Martin M,Sarkar U,Shao W,Stead D,Sumner N,Thakur K,Vasbinder MM,Varnes JG,Wang J,Wang L,Wu D,Wu L,Yang B,Yao T. (2020) Discovery of AZD4573, a Potent and Selective Inhibitor of CDK9 That Enables Short Duration of Target Engagement for the Treatment of Hematological Malignancies., 63 (24): [PMID:33306391] [10.1021/acs.jmedchem.0c01754] |
| 4. Huang Z, Wang T, Wang C, Fan Y.. (2022) CDK9 inhibitors in cancer research., 13 (6.0): [PMID:35814933] [10.1039/d2md00040g] |
| 5. Xu Z, Zhang B, Liu Z, Gou S.. (2022) Design, synthesis and anticancer evaluation of selective 2,4-disubstituted pyrimidine CDK9 inhibitors., 244 [PMID:36332552] [10.1016/j.ejmech.2022.114875] |
Source
Source(2):