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ID: ALA3628599
Max Phase: Preclinical
Molecular Formula: C23H21N5O3
Molecular Weight: 415.45
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CN1CCN(C(=O)c2cccc(Cn3nnc4c3C(=O)c3ccccc3C4=O)c2)CC1
Standard InChI: InChI=1S/C23H21N5O3/c1-26-9-11-27(12-10-26)23(31)16-6-4-5-15(13-16)14-28-20-19(24-25-28)21(29)17-7-2-3-8-18(17)22(20)30/h2-8,13H,9-12,14H2,1H3
Standard InChI Key: XHMWOYOVGULXFN-UHFFFAOYSA-N
Associated Targets(Human)
TDO2 Tchem Tryptophan 2,3-dioxygenase (1554 Activities)
IDO1 Tchem Indoleamine 2,3-dioxygenase (6650 Activities)
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PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
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OPRM1 Tclin Mu opioid receptor (19785 Activities)
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FLT3 Tclin Tyrosine-protein kinase receptor FLT3 (13481 Activities)
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CXCR4 Tclin C-X-C chemokine receptor type 4 (3338 Activities)
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AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
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CAT Tbio Catalase (7 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: 415.45 | Molecular Weight (Monoisotopic): 415.1644 | AlogP: 1.49 | #Rotatable Bonds: 3 |
| Polar Surface Area: 88.40 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 8 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 6.86 | CX LogP: 2.14 | CX LogD: 2.03 |
| Aromatic Rings: 3 | Heavy Atoms: 31 | QED Weighted: 0.50 | Np Likeness Score: -1.25 |
References
| 1. Wu JS, Lin SY, Liao FY, Hsiao WC, Lee LC, Peng YH, Hsieh CL, Wu MH, Song JS, Yueh A, Chen CH, Yeh SH, Liu CY, Lin SY, Yeh TK, Hsu JT, Shih C, Ueng SH, Hung MS, Wu SY.. (2015) Identification of Substituted Naphthotriazolediones as Novel Tryptophan 2,3-Dioxygenase (TDO) Inhibitors through Structure-Based Virtual Screening., 58 (19): [PMID:26348881] [10.1021/acs.jmedchem.5b00921] |
| 2. Huang R, Jing X, Huang X, Pan Y, Fang Y, Liang G, Liao Z, Wang H, Chen Z, Zhang Y.. (2020) Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3., 63 (4): [PMID:31999451] [10.1021/acs.jmedchem.9b01386] |
| 3. Pan S,Zhou Y,Wang Q,Wang Y,Tian C,Wang T,Huang L,Nan J,Li L,Yang S. (2020) Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)., 207 [PMID:32871341] [10.1016/j.ejmech.2020.112703] |
Source
Source(1):