Flavone
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Basic Info
| Common Name | Flavone(F05618) |
| 2D Structure | |
| Description | Quercetin is a flavonoid that forms the "backbone" for many other flavonoids, including the citrus flavonoids rutin, hesperidin, naringin and tangeritin. In studies, quercetin is found to be the most active of the flavonoids, and many medicinal plants owe much of their activity to their high quercetin content. Quercetin has demonstrated significant anti-inflammatory activity because of direct inhibition of several initial processes of inflammation. For example, it inhibits both the manufacture and release of histamine and other allergic/inflammatory mediators. In addition, it exerts potent antioxidant activity and vitamin C-sparing action. |
| FRCD ID | F05618 |
| CAS Number | 525-82-6 |
| PubChem CID | 10680 |
| Formula | C15H10O2 |
| IUPAC Name | 2-phenylchromen-4-one |
| InChI Key | VHBFFQKBGNRLFZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H |
| Canonical SMILES | C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2 |
| Isomeric SMILES | C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2 |
| Wikipedia | Flavone |
| Synonyms |
FLAVONE
525-82-6
2-Phenylchromone
2-Phenyl-4H-chromen-4-one
2-Phenyl-4-chromone
2-Phenyl-4-benzopyron
2-Phenyl-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-phenyl-
Asmacoril
Chromocor
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavones |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavone - Chromone - Benzopyran - 1-benzopyran - Pyranone - Benzenoid - Monocyclic benzene moiety - Pyran - Heteroaromatic compound - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 222.243 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 326 |
| Monoisotopic Mass | 222.068 |
| Exact Mass | 222.068 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9641 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8868 |
| P-glycoprotein Substrate | Non-substrate | 0.6558 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7379 |
| Non-inhibitor | 0.5145 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8370 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5940 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8090 |
| CYP450 2D6 Substrate | Non-substrate | 0.9124 |
| CYP450 3A4 Substrate | Non-substrate | 0.7084 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9644 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5201 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9372 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8993 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6321 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5396 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8858 |
| Non-inhibitor | 0.9350 | |
| AMES Toxicity | Non AMES toxic | 0.7310 |
| Carcinogens | Non-carcinogens | 0.9114 |
| Fish Toxicity | High FHMT | 0.8150 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9953 |
| Honey Bee Toxicity | High HBT | 0.7642 |
| Biodegradation | Not ready biodegradable | 0.7247 |
| Acute Oral Toxicity | III | 0.5110 |
| Carcinogenicity (Three-class) | Warning | 0.4507 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4247 | LogS |
| Caco-2 Permeability | 1.9246 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8447 | LD50, mol/kg |
| Fish Toxicity | 0.6694 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0088 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Immunomodulatory properties of quercetin-3-O-α-L-rhamnopyranoside from Rapaneamelanophloeos against influenza a virus. | BMC Complement Altern Med | 2018 Jun 15 | 29903008 |
| Oliveria decumbens essential oil: Chemical compositions and antimicrobialactivity against the growth of some clinical and standard strains causinginfection. | Microb Pathog | 2018 Jan | 29241765 |
| Analysis of proautophagic activities of Citrus flavonoids in liver cells reveals the superiority of a natural polyphenol mixture over pure flavones. | J Nutr Biochem | 2018 Aug | 29890411 |
| Antioxidant properties and anti-quorum sensing potential of Carum copticumessential oil and phenolics against Chromobacterium violaceum. | J Food Sci Technol | 2018 Aug | 30065392 |
| Genotype-by-environment effect on bioactive compounds in strawberry (Fragaria xananassa Duch.). | J Sci Food Agric | 2017 Sep | 28239870 |
| Promotion of Glucose Uptake in C2C12 Myotubes by Cereal Flavone Tricin and ItsUnderlying Molecular Mechanism. | J Agric Food Chem | 2017 May 17 | 28474889 |
| 6-Hydroxy-5,7-dimethoxy-flavone suppresses the neutrophil respiratory burst via selective PDE4 inhibition to ameliorate acute lung injury. | Free Radic Biol Med | 2017 May | 28263828 |
| Complementary cereals and legumes for health: Synergistic interaction of sorghum flavones and cowpea flavonols against LPS-induced inflammation in colonic myofibroblasts. | Mol Nutr Food Res | 2017 Jul | 28155259 |
| Activation of TRPV4 by dietary apigenin antagonizes renal fibrosis indeoxycorticosterone acetate (DOCA)-salt-induced hypertension. | Clin Sci (Lond) | 2017 Apr 1 | 28143892 |
| Total synthesis of 8-(6″-umbelliferyl)-apigenin and its analogs as anti-diabetic reagents. | Eur J Med Chem | 2016 Oct 21 | 27448923 |
| Anti-oxidative assays as markers for anti-inflammatory activity of flavonoids. | Int Immunopharmacol | 2016 Nov | 27598863 |
| Low hygroscopic spray-dried powders with trans-glycosylated food additivesenhance the solubility and oral bioavailability of ipriflavone. | Food Chem | 2016 Jan 1 | 26213075 |
| 7,8-Dihydroxyflavone reverses the depressive symptoms in mouse chronic mildstress. | Neurosci Lett | 2016 Dec 2 | 27773794 |
| Aqueous Extracts from Tunisian Diplotaxis: Phenol Content, Antioxidant andAnti-Acetylcholinesterase Activities, and Impact of Exposure to SimulatedGastrointestinal Fluids. | Antioxidants (Basel) | 2016 Apr 2 | 27049399 |
| The effects of apigenin on lipopolysaccharide-induced depressive-like behavior in mice. | Neurosci Lett | 2015 May 6 | 25800110 |
| Expression analysis of two P450 monooxygenase genes of the tobacco cutworm moth (Spodoptera litura) at different developmental stages and in response to plant allelochemicals. | J Chem Ecol | 2015 Jan | 25547988 |
| Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and TheirDerivatives. | J Agric Food Chem | 2015 Aug 5 | 26176501 |
| Dietary apigenin reduces LPS-induced expression of miR-155 restoring immune balance during inflammation. | Mol Nutr Food Res | 2015 Apr | 25641956 |
| Metabolomic fingerprint classification of Brachychiton acerifolius organs via UPLC-qTOF-PDA-MS analysis and chemometrics. | Nat Prod Res | 2015 | 25296242 |
| GmFNSII-controlled soybean flavone metabolism responds to abiotic stresses andregulates plant salt tolerance. | Plant Cell Physiol | 2014 Jan | 24192294 |
Targets
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Shimada T, Tanaka K, Takenaka S, Murayama N, Martin MV, Foroozesh MK, Yamazaki H, Guengerich FP, Komori M: Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35. doi: 10.1021/tx100286d. [21053930 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Han DH, Denison MS, Tachibana H, Yamada K: Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. Biosci Biotechnol Biochem. 2002 Jul;66(7):1479-87. [12224631 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRA
- Uniprot ID:
- P11474
- Molecular Weight:
- 45509.11 Da
References
- Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [14638870 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor, may regulate ESR1 transcriptional activity. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRB
- Uniprot ID:
- O95718
- Molecular Weight:
- 56207.085 Da
References
- Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [14638870 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Wang H, Li J, Gao Y, Xu Y, Pan Y, Tsuji I, Sun ZJ, Li XM: Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor. Asian J Androl. 2010 Jul;12(4):535-47. doi: 10.1038/aja.2010.14. Epub 2010 May 3. [20436506 ]
- General Function:
- Oxygen binding
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compounds to their activated forms, including polycyclic aromatic hydrocarbons. Promotes angiogenesis by removing cellular oxygenation products, thereby decreasing oxidative stress, release of antiangiogenic factor THBS2, then allowing endothelial cells migration, cell adhesion and capillary morphogenesis. These changes are concommitant with the endothelial nitric oxide synthase activity and nitric oxide synthesis. Plays an important role in the regulation of perivascular cell proliferation, migration, and survival through modulation of the intracellular oxidative state and NF-kappa-B expression and/or activity, during angiogenesis. Contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression.
- Gene Name:
- CYP1B1
- Uniprot ID:
- Q16678
- Molecular Weight:
- 60845.33 Da
References
- Shimada T, Tanaka K, Takenaka S, Foroozesh MK, Murayama N, Yamazaki H, Guengerich FP, Komori M: Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: a structure-function relationship study. Chem Res Toxicol. 2009 Jul;22(7):1325-33. doi: 10.1021/tx900127s. [19563207 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]