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ID: ALA8943
Max Phase: Preclinical
Molecular Formula: C20H22N2O5
Molecular Weight: 370.40
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(C[C@@H](Cc1cccc(O)c1)C(=O)N[C@H]1c2ccccc2C[C@H]1O)NO
Standard InChI: InChI=1S/C20H22N2O5/c23-15-6-3-4-12(9-15)8-14(11-18(25)22-27)20(26)21-19-16-7-2-1-5-13(16)10-17(19)24/h1-7,9,14,17,19,23-24,27H,8,10-11H2,(H,21,26)(H,22,25)/t14-,17-,19+/m1/s1
Standard InChI Key: VXDKQRWTOJFQKH-BJZITVGISA-N
Associated Targets(Human)
MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)
MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
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MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
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MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
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ADAMTS4 Tchem ADAMTS4 (425 Activities)
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ADAMTS5 Tchem ADAMTS5 (711 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: 370.40 | Molecular Weight (Monoisotopic): 370.1529 | AlogP: 1.22 | #Rotatable Bonds: 6 |
| Polar Surface Area: 118.89 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 5 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.79 | CX Basic pKa: | CX LogP: 1.22 | CX LogD: 1.20 |
| Aromatic Rings: 2 | Heavy Atoms: 27 | QED Weighted: 0.39 | Np Likeness Score: 0.41 |
References
| 1. Yao W, Chao M, Wasserman ZR, Liu RQ, Covington MB, Newton R, Christ D, Wexler RR, Decicco CP.. (2002) Potent P1' biphenylmethyl substituted aggrecanase inhibitors., 12 (1): [PMID:11738583] [10.1016/s0960-894x(01)00704-1] |
| 2. Yao W, Wasserman ZR, Chao M, Reddy G, Shi E, Liu RQ, Covington MB, Arner EC, Pratta MA, Tortorella M, Magolda RL, Newton R, Qian M, Ribadeneira MD, Christ D, Wexler RR, Decicco CP.. (2001) Design and synthesis of a series of (2R)-N(4)-hydroxy-2-(3-hydroxybenzyl)-N(1)- [(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide derivatives as potent, selective, and orally bioavailable aggrecanase inhibitors., 44 (21): [PMID:11585439] [10.1021/jm015533c] |
| 3. Cuffaro D, Ciccone L, Rossello A, Nuti E, Santamaria S.. (2022) Targeting Aggrecanases for Osteoarthritis Therapy: From Zinc Chelation to Exosite Inhibition., 65 (20.0): [PMID:36250680] [10.1021/acs.jmedchem.2c01177] |
Source
Source(1):