5,7-Dihydroxyflavone
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Basic Info
| Common Name | 5,7-Dihydroxyflavone(F05589) |
| 2D Structure | |
| Description | 5,7-Dihydroxyflavone is found in carrot. Chrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). Honeycomb also contains small amounts. It is also reported in Oroxylum indicum or Indian trumpetflower. (Wikipedia). |
| FRCD ID | F05589 |
| CAS Number | 480-40-0 |
| PubChem CID | 5281607 |
| Formula | C15H10O4 |
| IUPAC Name | 5,7-dihydroxy-2-phenylchromen-4-one |
| InChI Key | RTIXKCRFFJGDFG-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H |
| Canonical SMILES | C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O |
| Isomeric SMILES | C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O |
| Wikipedia | 5,7-Dihydroxyflavone |
| Synonyms |
5,7-Dihydroxyflavone
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-phenyl-
chrysin
480-40-0
Chrysine
5,7-Dihydroxy-2-phenyl-4H-chromen-4-one
Crysin
5,7-dihydroxy-2-phenylchromen-4-one
UNII-3CN01F5ZJ5
NSC-407436
|
| 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 | 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - 1-hydroxy-4-unsubstituted benzenoid - Benzenoid - Pyran - Monocyclic benzene moiety - Vinylogous acid - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - 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 | 254.241 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 384 |
| Monoisotopic Mass | 254.058 |
| Exact Mass | 254.058 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| 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+ | 0.6364 |
| Human Intestinal Absorption | HIA+ | 0.9887 |
| Caco-2 Permeability | Caco2+ | 0.8541 |
| P-glycoprotein Substrate | Non-substrate | 0.5073 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9543 |
| Non-inhibitor | 0.7525 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9037 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6655 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7813 |
| CYP450 2D6 Substrate | Non-substrate | 0.9126 |
| CYP450 3A4 Substrate | Non-substrate | 0.6907 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9222 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.7746 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7043 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.9580 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7316 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9559 |
| Non-inhibitor | 0.9098 | |
| AMES Toxicity | Non AMES toxic | 0.8906 |
| Carcinogens | Non-carcinogens | 0.9181 |
| Fish Toxicity | High FHMT | 0.8694 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9394 |
| Honey Bee Toxicity | High HBT | 0.7348 |
| Biodegradation | Not ready biodegradable | 0.8384 |
| Acute Oral Toxicity | III | 0.7012 |
| Carcinogenicity (Three-class) | Non-required | 0.6044 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7765 | LogS |
| Caco-2 Permeability | 0.8904 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6983 | LD50, mol/kg |
| Fish Toxicity | 0.8038 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3341 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The role of molecular modelling strategies in validating the effects of chrysinon sodium arsenite-induced chromosomal and DNA damage. | Hum Exp Toxicol | 2018 Jan 1:960327117751233 | 29308674 |
| Antioxidant, anti-inflammatory, and enzyme inhibitory activity of natural plant flavonoids and their synthesized derivatives. | J Biochem Mol Toxicol | 2018 Jan | 28972678 |
| Synthesis, characterization and xanthine oxidase inhibition of Cu(II)-chrysincomplex. | Spectrochim Acta A Mol Biomol Spectrosc | 2017 May 5 | 28167361 |
| Investigation of antiaromatase activity using hepatic microsomes of Nile tilapia (Oreochromis niloticus). | Drug Discov Ther | 2017 May 30 | 28320984 |
| Comparative studies on polyphenolic profile and antimicrobial activity ofpropolis samples selected from distinctive geographical areas of Hungary. | Food Sci Technol Int | 2017 Jun | 28595483 |
| Chrysin-induced sperm parameters and fatty acid profile changes improvereproductive performance of roosters. | Theriogenology | 2017 Dec | 28822243 |
| Chrysin ameliorates podocyte injury and slit diaphragm protein loss viainhibition of the PERK-eIF2α-ATF-CHOP pathway in diabetic mice. | Acta Pharmacol Sin | 2017 Aug | 28502979 |
| Chrysin induces brown fat-like phenotype and enhances lipid metabolism in 3T3-L1 adipocytes. | Nutrition | 2016 Sep | 27133810 |
| Preparation and activity evaluation of chrysin-β-D-galactopyranoside. | Arch Pharm Res | 2016 Oct | 27461029 |
| Role of dietary flavonoids in amelioration of sugar induced cataractogenesis. | Arch Biochem Biophys | 2016 Mar 1 | 26829674 |
| Dietary Compound Chrysin Inhibits Retinal Neovascularization with AbnormalCapillaries in db/db Mice. | Nutrients | 2016 Dec 3 | 27918469 |
| Use of active extracts of poplar buds against Penicillium italicum and possiblemodes of action. | Food Chem | 2016 Apr 1 | 26593534 |
| Effects of poplar buds as an alternative to propolis on postharvest diseasescontrol of strawberry fruits. | J Sci Food Agric | 2016 Apr | 26140351 |
| Inhibition of chrysin on xanthine oxidase activity and its inhibition mechanism. | Int J Biol Macromol | 2015 Nov | 26275460 |
| Use of ethyl lactate to extract bioactive compounds from Cytisus scoparius:Comparison of pressurized liquid extraction and medium scale ambient temperature systems. | Talanta | 2015 Aug 1 | 26048835 |
| Protective effects of the flavonoid chrysin against methylmercury-induced genotoxicity and alterations of antioxidant status, in vivo. | Oxid Med Cell Longev | 2015 | 25810809 |
| Ameliorative effect of chrysin on adenine-induced chronic kidney disease in rats. | PLoS One | 2015 | 25909514 |
| Formation of plasmonic silver nanoparticles by flavonoid reduction: A comparativestudy and application for determination of these substances. | Spectrochim Acta A Mol Biomol Spectrosc | 2015 | 26125987 |
| Phytochemical fingerprints of lime honey collected in serbia. | J AOAC Int | 2014 Sep-Oct | 25902974 |
| The antioxidant effect of the Malaysian Gelam honey on pancreatic hamster cellscultured under hyperglycemic conditions. | Clin Exp Med | 2014 May | 23584372 |
Targets
- 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
- Liu S, Abdelrahim M, Khan S, Ariazi E, Jordan VC, Safe S: Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells. Biol Chem. 2006 Sep;387(9):1209-13. [16972788 ]
- 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
- Liu S, Abdelrahim M, Khan S, Ariazi E, Jordan VC, Safe S: Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells. Biol Chem. 2006 Sep;387(9):1209-13. [16972788 ]
- General Function:
- Oxygen binding
- Specific Function:
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name:
- CYP19A1
- Uniprot ID:
- P11511
- Molecular Weight:
- 57882.48 Da
References
- Kao YC, Zhou C, Sherman M, Laughton CA, Chen S: Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study. Environ Health Perspect. 1998 Feb;106(2):85-92. [9435150 ]
- 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 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 ]
- Gene Name:
- TP53
- Uniprot ID:
- P04637
- Molecular Weight:
- 43652.79 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:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 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:
- Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
- Specific Function:
- Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
- Gene Name:
- NFE2L2
- Uniprot ID:
- Q16236
- Molecular Weight:
- 67825.9 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 that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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:
- 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, 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
- Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [9751507 ]