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ID: ALA421295
Max Phase: Preclinical
Molecular Formula: C15H13NO4
Molecular Weight: 271.27
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(/C=C/c1ccc(O)c(O)c1)Nc1ccccc1O
Standard InChI: InChI=1S/C15H13NO4/c17-12-4-2-1-3-11(12)16-15(20)8-6-10-5-7-13(18)14(19)9-10/h1-9,17-19H,(H,16,20)/b8-6+
Standard InChI Key: REGRZFZFPDDXIW-SOFGYWHQSA-N
Associated Targets(Human)
MMP-1/MMP-2 86 Activities
Matrix metalloproteinase 9 6779 Activities
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Matrix metalloproteinase-2 6627 Activities
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Matrix metalloproteinase-1 7046 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: 271.27 | Molecular Weight (Monoisotopic): 271.0845 | AlogP: 2.46 | #Rotatable Bonds: 3 |
| Polar Surface Area: 89.79 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.64 | CX Basic pKa: | CX LogP: 2.66 | CX LogD: 2.64 |
| Aromatic Rings: 2 | Heavy Atoms: 20 | QED Weighted: 0.51 | Np Likeness Score: -0.09 |
References
| 1. Rajan P, Vedernikova I, Cos P, Berghe DV, Augustyns K, Haemers A.. (2001) Synthesis and evaluation of caffeic acid amides as antioxidants., 11 (2): [PMID:11206462] [10.1016/s0960-894x(00)00630-2] |
| 2. Shi ZH, Li NG, Shi QP, Tang H, Tang YP, Li W, Yin L, Yang JP, Duan JA.. (2013) Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors., 23 (5): [PMID:23375794] [10.1016/j.bmcl.2013.01.027] |
Source
Source(1):