Anthraquinone
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Basic Info
| Common Name | Anthraquinone(F06250) |
| 2D Structure | |
| FRCD ID | F06250 |
| CAS Number | 84-65-1 |
| PubChem CID | 6780 |
| Formula | C14H8O2 |
| IUPAC Name | anthracene-9,10-dione |
| InChI Key | RZVHIXYEVGDQDX-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H |
| Canonical SMILES | C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3C2=O |
| Isomeric SMILES | C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3C2=O |
| Synonyms |
ANTHRAQUINONE
9,10-Anthraquinone
84-65-1
anthracene-9,10-dione
9,10-Anthracenedione
Anthradione
Hoelite
9,10-Dioxoanthracene
Corbit
Morkit
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Anthracenes |
| Subclass | Anthraquinones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Anthraquinones |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Anthraquinone - 9,10-anthraquinone - Aryl ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 208.216 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 261 |
| Monoisotopic Mass | 208.052 |
| Exact Mass | 208.052 |
| XLogP | 3.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.9653 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8682 |
| P-glycoprotein Substrate | Non-substrate | 0.6975 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7233 |
| Non-inhibitor | 0.8846 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8262 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7255 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7896 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.7148 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9357 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5919 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.6483 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6245 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9241 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7247 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9185 |
| Non-inhibitor | 0.9072 | |
| AMES Toxicity | AMES toxic | 0.8554 |
| Carcinogens | Non-carcinogens | 0.9132 |
| Fish Toxicity | High FHMT | 0.7544 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9875 |
| Honey Bee Toxicity | High HBT | 0.7268 |
| Biodegradation | Not ready biodegradable | 0.5648 |
| Acute Oral Toxicity | III | 0.4904 |
| Carcinogenicity (Three-class) | Non-required | 0.5893 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.2800 | LogS |
| Caco-2 Permeability | 1.8821 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7726 | LD50, mol/kg |
| Fish Toxicity | 0.6457 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.3267 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Apples (Crab apples/wild apples, Tejocotes,) | 0130010 | European Union | 0.01* | 18/05/2015 | |
| Quinces (Chinese quinces, Japanese quinces,) | 0130030 | European Union | 0.01* | 18/05/2015 | |
| Medlars | 0130040 | European Union | 0.01* | 18/05/2015 | |
| Loquats/Japanese medlars | 0130050 | European Union | 0.01* | 18/05/2015 | |
| Others (2) | 0130990 | European Union | 0.01* | 18/05/2015 | |
| Stone fruits | 0140000 | European Union | 0.01* | 18/05/2015 | |
| Apricots (Japanese apricots/Umes, Nectacots,) | 0140010 | European Union | 0.01* | 18/05/2015 | |
| Cherries (sweet) (Black cherries, Capulins, Chokecherries, Cornelian cherries/European corniols, Nanking cherries, Sour cherries/morello cherries,) | 0140020 | European Union | 0.01* | 18/05/2015 | |
| Peaches (Flat peaches/saturn peaches/paraguayas, Nectarines, Other hybrids of Persica vulgaris; syn: Prunus persica, not elsewhere mentioned,) | 0140030 | European Union | 0.01* | 18/05/2015 | |
| Others (2) | 0140990 | European Union | 0.01* | 18/05/2015 | |
| Berries and small fruits | 0150000 | European Union | 0.01* | 18/05/2015 | |
| (a) grapes | 0151000 | European Union | 0.01* | 18/05/2015 | |
| Table grapes (Kiwiberries/dwarf kiwi (2), Schisandra berries,) | 0151010 | European Union | 0.01* | 18/05/2015 | |
| Wine grapes (Amur river grapes, Muscadine grapes,) | 0151020 | European Union | 0.01* | 18/05/2015 | |
| (b) strawberries (Musky strawberries, Wild strawberries,) | 0152000 | European Union | 0.01* | 18/05/2015 | |
| (c) cane fruits | 0153000 | European Union | 0.01* | 18/05/2015 | |
| Blackberries | 0153010 | European Union | 0.01* | 18/05/2015 | |
| Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,) | 0153020 | European Union | 0.01* | 18/05/2015 | |
| Raspberries (red and yellow) (Arctic brambles/arctic raspberries/nectar berries, Black raspberries, Korean black raspberries, Korean raspberries, Nectar raspberries, Wineberries/Japanese wineberries,) | 0153030 | European Union | 0.01* | 18/05/2015 | |
| Others (2) | 0153990 | European Union | 0.01* | 18/05/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| An ultrasensitive hollow-silica-based biosensor for pathogenic Escherichia coliDNA detection. | Anal Bioanal Chem | 2018 Mar | 29504083 |
| Anthraquinone and naphthopyrone glycosides from Cassia obtusifolia seeds mediate hepatoprotection via Nrf2-mediated HO-1 activation and MAPK modulation. | Arch Pharm Res | 2018 Jun | 29804278 |
| Aurantio-obtusin, an anthraquinone from cassiae semen, ameliorates lung inflammatory responses. | Phytother Res | 2018 Aug | 29675883 |
| Direct Effects of Physcion, Chrysophanol, Emodin, and Pachybasin on Germinationand Appressorium Formation of the Barley ( Hordeum vulgare L.) Powdery MildewFungus Blumeria graminis f. sp. hordei (DC.) Speer. | J Agric Food Chem | 2018 Apr 4 | 29554805 |
| Interaction of anthraquinones of <i>Cassia occidentalis</i> seeds with DNA and Glutathione. | Toxicol Rep | 2018 | 29326881 |
| Spiroketalcarminic Acid, a Novel Minor Anthraquinone Pigment in Cochineal ExtractUsed in Food Additives. | Chem Pharm Bull (Tokyo) | 2017 Sep 1 | 28674282 |
| Toxicity of Senna occidentalis seeds in laying hens and its effects on egg production. | Avian Pathol | 2017 Jun | 28161970 |
| Structure-Antioxidative and Anti-Inflammatory Activity Relationships of Purpurin and Related Anthraquinones in Chemical and Cell Assays. | Molecules | 2017 Feb 10 | 28208613 |
| Molecular basis for the DNA damage induction and anticancer activity of asymmetrically substituted anthrapyridazone PDZ-7. | Oncotarget | 2017 Dec 1 | 29285240 |
| Review of anthraquinone applications for pest management and agricultural cropprotection. | Pest Manag Sci | 2016 Oct | 27252044 |
| Immunomodulatory potential of Rhein, an anthraquinone moiety of Cassia occidentalis seeds. | Toxicol Lett | 2016 Mar 14 | 26784856 |
| European medicinal and edible plants associated with subacute and chronic toxicity part I: Plants with carcinogenic, teratogenic and endocrine-disrupting effects. | Food Chem Toxicol | 2016 Jun | 27090581 |
| Emodin improves lipid and glucose metabolism in high fat diet-induced obese mice through regulating SREBP pathway. | Eur J Pharmacol | 2016 Jan 5 | 26626587 |
| Exploration of industrially important pigments from soil fungi. | Appl Microbiol Biotechnol | 2016 Feb | 26701360 |
| Identification and characterization of the ergochrome gene cluster in the plant pathogenic fungus <i>Claviceps purpurea</i>. | Fungal Biol Biotechnol | 2016 | 28955461 |
| Determinations for Pesticides on Black, Green, Oolong, and White Teas by GasChromatography Triple-Quadrupole Mass Spectrometry. | J Agric Food Chem | 2015 Sep 23 | 26209005 |
| Development of the dichlorvos-ammonia (DV-AM) method for the visual detection of aflatoxigenic fungi. | Appl Microbiol Biotechnol | 2015 Dec | 26300294 |
| Bird-repellent effects on bait efficacy for control of invasive mammal pests. | Pest Manag Sci | 2015 Aug | 25143303 |
| Functional characterization of a veA-dependent polyketide synthase gene in Aspergillus flavus necessary for the synthesis of asparasone, a sclerotium-specific pigment. | Fungal Genet Biol | 2014 Mar | 24412484 |
| Effects of several quinones on insulin aggregation. | Sci Rep | 2014 Jul 10 | 25008537 |