Quinone
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Quinone(F05461) |
| 2D Structure | |
| Description | Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world. |
| FRCD ID | F05461 |
| CAS Number | 106-51-4 |
| PubChem CID | 4650 |
| Formula | C6H4O2 |
| IUPAC Name | cyclohexa-2,5-diene-1,4-dione |
| InChI Key | AZQWKYJCGOJGHM-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H |
| Canonical SMILES | C1=CC(=O)C=CC1=O |
| Isomeric SMILES | C1=CC(=O)C=CC1=O |
| Wikipedia | Quinone |
| Synonyms |
1,4-BENZOQUINONE
p-benzoquinone
Benzoquinone
Quinone
106-51-4
p-Quinone
Chinone
2,5-Cyclohexadiene-1,4-dione
Cyclohexadienedione
para-Quinone
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Ketones - Cyclic ketones - Quinones - Benzoquinones |
| Direct Parent | P-benzoquinones |
| Alternative Parents | |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | P-benzoquinone - Organic oxide - Hydrocarbon derivative - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 108.096 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 149 |
| Monoisotopic Mass | 108.021 |
| Exact Mass | 108.021 |
| XLogP | 0.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| 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+ | 0.9611 |
| Human Intestinal Absorption | HIA+ | 0.9973 |
| Caco-2 Permeability | Caco2+ | 0.8423 |
| P-glycoprotein Substrate | Non-substrate | 0.8285 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8618 |
| Non-inhibitor | 0.9656 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8655 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7591 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8224 |
| CYP450 2D6 Substrate | Non-substrate | 0.9244 |
| CYP450 3A4 Substrate | Non-substrate | 0.7518 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9149 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9311 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9133 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8933 |
| Non-inhibitor | 0.9862 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.7986 |
| Fish Toxicity | Low FHMT | 0.5852 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9442 |
| Honey Bee Toxicity | High HBT | 0.8207 |
| Biodegradation | Ready biodegradable | 0.7273 |
| Acute Oral Toxicity | II | 0.7537 |
| Carcinogenicity (Three-class) | Non-required | 0.6638 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.9279 | LogS |
| Caco-2 Permeability | 1.7819 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8887 | LD50, mol/kg |
| Fish Toxicity | 1.3110 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6020 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Isothiocyanates and Xenobiotic Detoxification. | Mol Nutr Food Res | 2018 Sep | 29288567 |
| Screening of potential bioremediation enzymes from hot spring bacteria using conventional plate assays and liquid chromatography - Tandem mass spectrometry (Lc-Ms/Ms). | J Environ Manage | 2018 Oct 1 | 29986326 |
| Identification and analysis of the reactive metabolites related to the hepatotoxicity of safrole. | Xenobiotica | 2018 Nov | 29082813 |
| Photodegradation of Dicloran in Freshwater and Seawater. | J Agric Food Chem | 2018 Mar 21 | 29474091 |
| Fluorometric determination of dopamine by using molybdenum disulfide quantumdots. | Mikrochim Acta | 2018 Mar 20 | 29594717 |
| Strecker Aldehyde Formation in Wine: New Insights into the Role of Gallic Acid,Glucose, and Metals in Phenylacetaldehyde Formation. | J Agric Food Chem | 2018 Mar 14 | 28238260 |
| Anti-inflammatory Activity of 8-Hydroxydaidzein in LPS-Stimulated BV2 Microglial Cells via Activation of Nrf2-Antioxidant and Attenuation of Akt/NF-κB-Inflammatory Signaling Pathways, as Well As Inhibition of COX-2 Activity. | J Agric Food Chem | 2018 Jun 13 | 29790749 |
| Grape seed procyanidin extract protects against Pb-induced lung toxicity byactivating the AMPK/Nrf2/p62 signaling axis. | Food Chem Toxicol | 2018 Jun | 29630945 |
| Identifying Plant Stress Responses to Roxarsone in Soybean Root Exudates: NewInsights from Two-Dimensional Correlation Spectroscopy. | J Agric Food Chem | 2018 Jan 10 | 29240415 |
| Alleviation of cadmium-induced oxidative stress by trehalose via inhibiting theNrf2-Keap1 signaling pathway in primary rat proximal tubular cells. | J Biochem Mol Toxicol | 2018 Jan | 29140578 |
| Two-dimensional MoS2 as a nano-binder for ssDNA: Ultrasensitive aptamer basedamperometric detection of Ochratoxin A. | Mikrochim Acta | 2018 Feb 7 | 29594615 |
| Eco-friendly green synthesis of Ag@Fe bimetallic nanoparticles: Antioxidant,antimicrobial and photocatalytic degradation of bromothymol blue. | J Photochem Photobiol B | 2018 Aug | 29906655 |
| Fitness, Competitive Ability, and Mutation Stability of Isolates ofColletotrichum acutatum from Strawberry Resistant to QoI Fungicides. | Phytopathology | 2018 Apr | 29135359 |
| Chemotaxonomy of Mycotoxigenic Small-Spored <i>Alternaria</i> Fungi - Do Multitoxin Mixtures Act as an Indicator for Species Differentiation? | Front Microbiol | 2018 | 30018598 |
| Chemotherapy-Induced Tissue Injury: An Insight into the Role of Extracellular Vesicles-Mediated Oxidative Stress Responses. | Antioxidants (Basel) | 2017 Sep 28 | 28956814 |
| Naphtho[1,2-b]furan-4,5-dione is a potent anti-MRSA agent against planktonic,biofilm and intracellular bacteria. | Future Microbiol | 2017 Sep | 28799789 |
| Phenethyl isothiocyanate protects against H2O2-induced insulin resistance in3T3-L1 adipocytes. | Biosci Biotechnol Biochem | 2017 Nov | 28899227 |
| The role of oxidative stress in DNA damage in pancreatic β cells induced by di-(2-ethylhexyl) phthalate. | Chem Biol Interact | 2017 Mar 1 | 28115068 |
| Dietary luteolin attenuates chronic liver injury induced by mercuric chloride via the Nrf2/NF-κB/P53 signaling pathway in rats. | Oncotarget | 2017 Jun 20 | 28498799 |
| Massilia chloroacetimidivorans sp. nov., a chloroacetamide herbicide-degradingbacterium isolated from soil. | Antonie Van Leeuwenhoek | 2017 Jun | 28434178 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Endopeptidase activity
- Specific Function:
- Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cleaves and activates sterol regulatory element binding proteins (SREBPs). Can also promote apoptosis.
- Gene Name:
- CASP1
- Uniprot ID:
- P29466
- Molecular Weight:
- 45158.215 Da
References
- Huang FC, Chan WK, Moriarty KJ, Zhang DC, Chang MN, He W, Yu KT, Zilberstein A: Novel cytokine release inhibitors. Part I: Triterpenes. Bioorg Med Chem Lett. 1998 Jul 21;8(14):1883-6. [9873452 ]
- General Function:
- Methylumbelliferyl-acetate deacetylase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
- Gene Name:
- CES2
- Uniprot ID:
- O00748
- Molecular Weight:
- 61806.41 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Ubiquitin binding
- Specific Function:
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
- Gene Name:
- TOP2A
- Uniprot ID:
- P11388
- Molecular Weight:
- 174383.88 Da
References
- Gurbani D, Kukshal V, Laubenthal J, Kumar A, Pandey A, Tripathi S, Arora A, Jain SK, Ramachandran R, Anderson D, Dhawan A: Mechanism of inhibition of the ATPase domain of human topoisomerase IIalpha by 1,4-benzoquinone, 1,2-naphthoquinone, 1,4-naphthoquinone, and 9,10-phenanthroquinone. Toxicol Sci. 2012 Apr;126(2):372-90. doi: 10.1093/toxsci/kfr345. Epub 2012 Jan 4. [22218491 ]
- Specific Function:
- Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
- Gene Name:
- FBF1
- Uniprot ID:
- Q8TES7
- Molecular Weight:
- 125445.19 Da
References
- Lin YS, Vermeulen R, Tsai CH, Waidyanatha S, Lan Q, Rothman N, Smith MT, Zhang L, Shen M, Li G, Yin S, Kim S, Rappaport SM: Albumin adducts of electrophilic benzene metabolites in benzene-exposed and control workers. Environ Health Perspect. 2007 Jan;115(1):28-34. [17366815 ]
- General Function:
- Triglyceride lipase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
- Gene Name:
- CES1
- Uniprot ID:
- P23141
- Molecular Weight:
- 62520.62 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Protein tyrosine phosphatase activity
- Specific Function:
- Tyrosine protein phosphatase which functions as a dosage-dependent inducer of mitotic progression. Required for G2/M phases of the cell cycle progression and abscission during cytokinesis in a ECT2-dependent manner. Directly dephosphorylates CDK1 and stimulates its kinase activity. The three isoforms seem to have a different level of activity.
- Gene Name:
- CDC25B
- Uniprot ID:
- P30305
- Molecular Weight:
- 64986.745 Da
References
- Cao S, Murphy BT, Foster C, Lazo JS, Kingston DG: Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases. Bioorg Med Chem. 2009 Mar 15;17(6):2276-81. doi: 10.1016/j.bmc.2008.10.090. Epub 2008 Nov 8. [19028102 ]
- General Function:
- Zinc ion binding
- Specific Function:
- DNA deaminase (cytidine deaminase) which acts as an inhibitor of retrovirus replication and retrotransposon mobility via deaminase-dependent and -independent mechanisms. Exhibits potent antiviral activity against vif-deficient HIV-1. After the penetration of retroviral nucleocapsids into target cells of infection and the initiation of reverse transcription, it can induce the conversion of cytosine to uracil in the minus-sense single-strand viral DNA, leading to G-to-A hypermutations in the subsequent plus-strand viral DNA. The resultant detrimental levels of mutations in the proviral genome, along with a deamination-independent mechanism that works prior to the proviral integration, together exert efficient antiretroviral effects in infected target cells. Selectively targets single-stranded DNA and does not deaminate double-stranded DNA or single-or double-stranded RNA. Exhibits antiviral activity also against simian immunodeficiency viruses (SIVs), hepatitis B virus (HBV), equine infectious anemia virus (EIAV), xenotropic MuLV-related virus (XMRV) and simian foamy virus (SFV). May inhibit the mobility of LTR and non-LTR retrotransposons.
- Gene Name:
- APOBEC3G
- Uniprot ID:
- Q9HC16
- Molecular Weight:
- 46407.605 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
- General Function:
- Vascular endothelial growth factor-activated receptor activity
- Specific Function:
- Tyrosine-protein kinase that acts as a cell-surface receptor for VEGFA, VEGFC and VEGFD. Plays an essential role in the regulation of angiogenesis, vascular development, vascular permeability, and embryonic hematopoiesis. Promotes proliferation, survival, migration and differentiation of endothelial cells. Promotes reorganization of the actin cytoskeleton. Isoforms lacking a transmembrane domain, such as isoform 2 and isoform 3, may function as decoy receptors for VEGFA, VEGFC and/or VEGFD. Isoform 2 plays an important role as negative regulator of VEGFA- and VEGFC-mediated lymphangiogenesis by limiting the amount of free VEGFA and/or VEGFC and preventing their binding to FLT4. Modulates FLT1 and FLT4 signaling by forming heterodimers. Binding of vascular growth factors to isoform 1 leads to the activation of several signaling cascades. Activation of PLCG1 leads to the production of the cellular signaling molecules diacylglycerol and inositol 1,4,5-trisphosphate and the activation of protein kinase C. Mediates activation of MAPK1/ERK2, MAPK3/ERK1 and the MAP kinase signaling pathway, as well as of the AKT1 signaling pathway. Mediates phosphorylation of PIK3R1, the regulatory subunit of phosphatidylinositol 3-kinase, reorganization of the actin cytoskeleton and activation of PTK2/FAK1. Required for VEGFA-mediated induction of NOS2 and NOS3, leading to the production of the signaling molecule nitric oxide (NO) by endothelial cells. Phosphorylates PLCG1. Promotes phosphorylation of FYN, NCK1, NOS3, PIK3R1, PTK2/FAK1 and SRC.
- Gene Name:
- KDR
- Uniprot ID:
- P35968
- Molecular Weight:
- 151525.555 Da
References
- Wissner A, Floyd MB, Johnson BD, Fraser H, Ingalls C, Nittoli T, Dushin RG, Discafani C, Nilakantan R, Marini J, Ravi M, Cheung K, Tan X, Musto S, Annable T, Siegel MM, Loganzo F: 2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as covalent-binding, irreversible inhibitors of the kinase domain of vascular endothelial growth factor receptor-2. J Med Chem. 2005 Dec 1;48(24):7560-81. [16302797 ]