| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:11:29 UTC |
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| Update date | 2019-11-26 03:10:48 UTC |
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| Primary ID | FDB014814 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Carnosol |
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| Description | Bitter principle in Salvia carnosa, Salvia officinalis (sage), Salvia triloba (Greek sage) and Rosmarinus officinalis (rosemary). Nutriceutical with anticancer props.
Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has multiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellular signal-regulated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462); Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665) |
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| CAS Number | 5957-80-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 1,3,4,9,10,10AS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4ar-(epoxymethano)phenanthren-12-one | HMDB | | 11,12-Dihydroxy-8,11,13-abietatrien-20,7-olide | db_source | | Picrosalvin | db_source |
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| Predicted Properties | |
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| Chemical Formula | C20H26O4 |
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| IUPAC name | 3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one |
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| InChI Identifier | InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3 |
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| InChI Key | XUSYGBPHQBWGAD-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1CC2OC3=O |
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| Average Molecular Weight | 330.418 |
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| Monoisotopic Molecular Weight | 330.18310932 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Terpene lactones |
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| Direct Parent | Diterpene lactones |
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| Alternative Parents | |
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| Substituents | - Diterpene lactone
- Diterpenoid
- Phenanthrene
- Benzopyran
- Isochromane
- 2-benzopyran
- Tetralin
- 1-hydroxy-4-unsubstituted benzenoid
- Delta valerolactone
- Delta_valerolactone
- Benzenoid
- Oxane
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 72.70%; H 7.93%; O 19.37% | DFC |
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| Melting Point | Mp 221-226° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]D -66 (EtOH) | DFC |
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| Spectroscopic UV Data | 283 (e 2510) (EtOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0019000000-08dcb84c59b0d280b13f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001r-6097000000-b2894527af41d8c29ad8 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-067l-9041000000-63e8a7af26ccd9f942f7 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0009000000-a5b241b8344c36c2f0bf | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0019000000-e7accf1a4d2c8280c2f4 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03y0-1093000000-a5175230ca7dfd038446 | 2016-08-03 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 390568 |
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| ChEMBL ID | CHEMBL218693 |
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| KEGG Compound ID | C09069 |
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| Pubchem Compound ID | 442009 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 668 |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02121 |
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| CRC / DFC (Dictionary of Food Compounds) ID | JWJ41-W:JWJ41-W |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | PICROSALVIN|CARNOSOL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003410 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| 5-lipoxygenase inhibitor | 23924 | An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes. | DUKE | | Antibiotic | 22582 | An agent that inhibits the growth of or destroys microorganisms, particularly bacteria. Therapeutically, antibiotics are used to treat bacterial infections, such as pneumonia, tuberculosis, and skin infections, by targeting specific biochemical processes essential for microbial survival. | DUKE | | Anti hepatotoxic | 62868 | An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins. | DUKE | | Anti HIV | 22587 | An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression. | DUKE | | Anti-inflammatory | 35472 | An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis. | DUKE | | Anti lipoperoxidant | | An agent that prevents peroxidation of lipids, reducing oxidative stress and cell damage. Its biological role involves protecting cell membranes from degradation. Therapeutically, it has applications in managing conditions related to oxidative stress, with key medical uses including neuroprotection, anti-inflammation, and antioxidant therapy. | DUKE | | Anti-mutagenic | | An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects. | DUKE | | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | | Anti radicular | | An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management. | DUKE | | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | | Antitumor promoter | 35610 | An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis. | DUKE | | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | | Candidicide | | An agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases. | DUKE | | Cyclooxygenase inhibitor | 35544 | An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation. | DUKE | | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | | Metal chelator | 38161 | An agent that binds to metal ions, reducing their toxicity and availability. It plays a biological role in regulating metal ion homeostasis and has therapeutic applications in treating metal poisoning, iron overload, and neurodegenerative diseases, with key medical uses including Wilson's disease and hemochromatosis management. | DUKE | | Ornithine-decarboxylase inhibitor | 23924 | An agent that blocks the activity of ornithine decarboxylase, an enzyme involved in cell growth and proliferation. It reduces polyamine synthesis, inhibiting tumor growth and proliferation. Therapeutically, it is used to treat cancer, particularly in combination with other therapies, and has potential applications in managing parasitic infections and skin disorders. | DUKE | | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | | Protease inhibitor | 37670 | An agent that blocks the activity of proteases, enzymes that break down proteins. It has therapeutic applications in treating viral infections, cancer, and genetic disorders, with key medical uses including HIV/AIDS management and hepatitis C treatment. | DUKE | | Quinone-reductase inducer | | An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | | Flavor | Citations |
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| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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