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ID: ALA484663
Max Phase: Preclinical
Molecular Formula: C15H10O4
Molecular Weight: 254.24
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): 6,4'-Dihydroxyflavone
Synonyms from Alternative Forms(1):
Canonical SMILES: O=c1cc(-c2ccc(O)cc2)oc2ccc(O)cc12
Standard InChI: InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)15-8-13(18)12-7-11(17)5-6-14(12)19-15/h1-8,16-17H
Standard InChI Key: FFULTBKXWHYHFQ-UHFFFAOYSA-N
Associated Targets(Human)
Tyrosine-protein kinase LCK 9212 Activities
Peroxisome proliferator-activated receptor gamma 15191 Activities
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Peroxisome proliferator-activated receptor alpha 9197 Activities
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Prelamin-A/C 36751 Activities
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microRNA 21 64692 Activities
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Ras-related protein Rab-9A 22488 Activities
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Survival motor neuron protein 34246 Activities
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Thyroid hormone receptor beta-1 7926 Activities
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Microtubule-associated protein tau 95507 Activities
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Arachidonate 15-lipoxygenase 7108 Activities
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Niemann-Pick C1 protein 18985 Activities
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15-hydroxyprostaglandin dehydrogenase [NAD+] 24926 Activities
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Cellular tumor antigen p53 48468 Activities
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Cytochrome P450 3A4 53859 Activities
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Beta-glucocerebrosidase 14647 Activities
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Sentrin-specific protease 8 1687 Activities
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Sentrin-specific protease 7 1073 Activities
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Sentrin-specific protease 6 1074 Activities
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ATPase family AAA domain-containing protein 5 122566 Activities
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Importin subunit beta-1/Snurportin-1 25097 Activities
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Flap endonuclease 1 12055 Activities
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HepG2 196354 Activities
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Caspase-3 3632 Activities
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HEK293 82097 Activities
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Glucagon-like peptide 1 receptor 111429 Activities
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Breast cancer type 1 susceptibility protein 15908 Activities
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Guanine nucleotide-binding protein G(s), subunit alpha 103405 Activities
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Peroxisome proliferator-activated receptor delta 6293 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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Inositol hexakisphosphate kinase 2 79 Activities
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Inositol polyphosphate multikinase 34 Activities
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Associated Targets(non-human)
Aldose reductase 4007 Activities
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Nuclear receptor ROR-gamma 89407 Activities
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Plasmodium falciparum 966862 Activities
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Luciferin 4-monooxygenase 66902 Activities
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Molecule Features
| Natural Product: Yes | 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: 254.24 | Molecular Weight (Monoisotopic): 254.0579 | AlogP: 2.87 | #Rotatable Bonds: 1 |
| Polar Surface Area: 70.67 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.58 | CX Basic pKa: | CX LogP: 2.36 | CX LogD: 2.33 |
| Aromatic Rings: 3 | Heavy Atoms: 19 | QED Weighted: 0.70 | Np Likeness Score: 0.79 |
References
| 1. Cushman M, Nagarathnam D, Geahlen RL.. (1991) Synthesis and evaluation of hydroxylated flavones and related compounds as potential inhibitors of the protein-tyrosine kinase p56lck., 54 (5): [PMID:1800636] [10.1021/np50077a018] |
| 2. Chang CJ, Geahlen RL.. (1992) Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents., 55 (11): [PMID:1479375] [10.1021/np50089a001] |
| 3. Mercader AG, Duchowicz PR, Fernández FM, Castro EA, Bennardi DO, Autino JC, Romanelli GP.. (2008) QSAR prediction of inhibition of aldose reductase for flavonoids., 16 (15): [PMID:18585047] [10.1016/j.bmc.2008.06.004] |
| 4. Matin A, Gavande N, Kim MS, Yang NX, Salam NK, Hanrahan JR, Roubin RH, Hibbs DE.. (2009) 7-Hydroxy-benzopyran-4-one derivatives: a novel pharmacophore of peroxisome proliferator-activated receptor alpha and -gamma (PPARalpha and gamma) dual agonists., 52 (21): [PMID:19807106] [10.1021/jm900964r] |
| 5. PubChem BioAssay data set, |
| 6. PubChem BioAssay data set, |
| 7. Matin A, Doddareddy MR, Gavande N, Nammi S, Groundwater PW, Roubin RH, Hibbs DE.. (2013) The discovery of novel isoflavone pan peroxisome proliferator-activated receptor agonists., 21 (3): [PMID:23265844] [10.1016/j.bmc.2012.11.040] |
| 8. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds, [10.6019/CHEMBL3301361] |
| 9. Gu C, Stashko MA, Puhl-Rubio AC, Chakraborty M, Chakraborty A, Frye SV, Pearce KH, Wang X, Shears SB, Wang H.. (2019) Inhibition of Inositol Polyphosphate Kinases by Quercetin and Related Flavonoids: A Structure-Activity Analysis., 62 (3): [PMID:30624931] [10.1021/acs.jmedchem.8b01593] |
Source
Source(3):