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ID: ALA245952
Max Phase: Preclinical
Molecular Formula: C16H18O4
Molecular Weight: 274.32
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Oc1ccc(CCCCc2ccc(O)c(O)c2)cc1O
Standard InChI: InChI=1S/C16H18O4/c17-13-7-5-11(9-15(13)19)3-1-2-4-12-6-8-14(18)16(20)10-12/h5-10,17-20H,1-4H2
Standard InChI Key: JMYXNUMGPRHHBC-UHFFFAOYSA-N
Associated Targets(Human)
Insulin-like growth factor I receptor 8605 Activities
MCF7 126967 Activities
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Arachidonate 15-lipoxygenase 7108 Activities
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NCI-H69 709 Activities
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Associated Targets(non-human)
Acriflavine resistance protein B 1424 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: 274.32 | Molecular Weight (Monoisotopic): 274.1205 | AlogP: 3.07 | #Rotatable Bonds: 5 |
| Polar Surface Area: 80.92 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.21 | CX Basic pKa: | CX LogP: 4.18 | CX LogD: 4.18 |
| Aromatic Rings: 2 | Heavy Atoms: 20 | QED Weighted: 0.50 | Np Likeness Score: 0.53 |
References
| 1. Blecha JE, Anderson MO, Chow JM, Guevarra CC, Pender C, Penaranda C, Zavodovskaya M, Youngren JF, Berkman CE.. (2007) Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs., 17 (14): [PMID:17502145] [10.1016/j.bmcl.2007.04.092] |
| 2. Ho SS, Go ML.. (2013) Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity., 23 (22): [PMID:24080463] [10.1016/j.bmcl.2013.09.014] |
| 3. Asiamah I, Hodgson HL, Maloney K, Allen KJ, Krol ES.. (2015) Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues., 23 (21): [PMID:26439661] [10.1016/j.bmc.2015.09.039] |
| 4. Wang Y,Alenzy R,Song D,Liu X,Teng Y,Mowla R,Ma Y,Polyak SW,Venter H,Ma S. (2020) Structural optimization of natural product nordihydroguaretic acid to discover novel analogues as AcrB inhibitors., 186 [PMID:31801655] [10.1016/j.ejmech.2019.111910] |
Source
Source(1):