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ID: ALA498272
Max Phase: Preclinical
Molecular Formula: C20H17NO3S
Molecular Weight: 351.43
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1occ(O)c(=S)c1C(=O)NCc1ccc(-c2ccccc2)cc1
Standard InChI: InChI=1S/C20H17NO3S/c1-13-18(19(25)17(22)12-24-13)20(23)21-11-14-7-9-16(10-8-14)15-5-3-2-4-6-15/h2-10,12,22H,11H2,1H3,(H,21,23)
Standard InChI Key: NSHZQFVEIUWJLE-UHFFFAOYSA-N
Associated Targets(Human)
MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)
MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
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MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
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MMP9 Tchem Matrix metalloproteinase 9 (6779 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: 351.43 | Molecular Weight (Monoisotopic): 351.0929 | AlogP: 4.62 | #Rotatable Bonds: 4 |
| Polar Surface Area: 62.47 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 10.48 | CX Basic pKa: | CX LogP: 3.81 | CX LogD: 3.81 |
| Aromatic Rings: 3 | Heavy Atoms: 25 | QED Weighted: 0.67 | Np Likeness Score: -0.58 |
References
| 1. Yan YL, Miller MT, Cao Y, Cohen SM.. (2009) Synthesis of hydroxypyrone- and hydroxythiopyrone-based matrix metalloproteinase inhibitors: developing a structure-activity relationship., 19 (7): [PMID:19261472] [10.1016/j.bmcl.2009.02.044] |
| 2. Arshad JZ, Hanif M.. (2022) Hydroxypyrone derivatives in drug discovery: from chelation therapy to rational design of metalloenzyme inhibitors., 13 (10.0): [PMID:36325396] [10.1039/d2md00175f] |
Source
Source(1):