| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:09:45 UTC |
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| Update date | 2019-11-26 03:05:10 UTC |
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| Primary ID | FDB011636 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Ajoene |
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| Description | Isolated from garlic (Allium sativum) extracts. Nutriceutical with anti-cancer props.
Ajoene (pronounced /???ho?i?n/) is a chemical compound available from garlic (Allium sativum). The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of two isomers, E-, and Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.; Ajoene, an unsaturated disulfide, is formed from the bonding of three allicin molecules. Allicin is a sulfinyl compound that gives garlic its strong odor and flavor. The release of allicin occurs after a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil). |
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| CAS Number | 92285-01-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9CI | db_source | | 2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfide | biospider | | 4,5,9-Trithia-1,6,11-dodecatriene 9-oxide | db_source | | 4,5,9-Trithiadodeca-1,6,11-triene 9-oxide | biospider | | Ajoene, trans- | biospider | | Allyl 3-allylsulfinyl-1-propenyl disulfide | db_source | | Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenyl | biospider | | Trans-ajoene | biospider |
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| Predicted Properties | |
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| Chemical Formula | C9H14OS3 |
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| IUPAC name | 3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene |
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| InChI Identifier | InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5- |
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| InChI Key | IXELFRRANAOWSF-ALCCZGGFSA-N |
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| Isomeric SMILES | C=CCSS\C=C/CS(=O)CC=C |
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| Average Molecular Weight | 234.402 |
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| Monoisotopic Molecular Weight | 234.02067714 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H). |
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| Kingdom | Organic compounds |
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| Super Class | Organosulfur compounds |
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| Class | Sulfoxides |
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| Sub Class | Not Available |
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| Direct Parent | Sulfoxides |
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| Alternative Parents | |
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| Substituents | - Allyl sulfur compound
- Sulfoxide
- Organic disulfide
- Sulfenyl compound
- Sulfinyl compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic 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 - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 46.12%; H 6.02%; O 6.83%; S 41.04% | DFC |
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| Melting Point | Not Available | |
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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 | Not Available | |
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| Spectroscopic UV Data | [neutral] lmax 240 () (MeOH) (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 | Not Available |
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| External Links |
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| ChemSpider ID | 8056824 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C16757 |
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| Pubchem Compound ID | 9881148 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB33566 |
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| CRC / DFC (Dictionary of Food Compounds) ID | GWS23-E:GWS23-E |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | TRANS-AJOENE|TRANS-CIS-AJOENE|AJOENE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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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 | Ajoene |
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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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| anti aggregant | | | DUKE | | anti allergic | 50857 | A drug used to treat allergic reactions. | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti HIV | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti leukotriene | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti lymphomic | | | DUKE | | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti metastatic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti mutagenic | | | DUKE | | anti mycotic | | | DUKE | | anti platelet | | | DUKE | | anti proliferant | | | DUKE | | anti prostaglandin | 49020 | A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti stomatitic | | | DUKE | | anti thrombotic | 50248 | Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. | DUKE | | anti trypanosomic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | apoptotic | | | DUKE | | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | | candidicide | | | DUKE | | candidistat | | | DUKE | | cyclooxygenase-2 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | | cytostatic | | | DUKE | | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | fungistat | | | DUKE | | Gram(+)icide | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | Gram(-)icide | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | hypocholesterolemic | | | DUKE | | lipolytic | | | DUKE | | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | | NF-kappa-B inducer | | | DUKE | | nitric-oxide inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | prostaglandin inhibitor | 49023 | A compound that inhibits the action of prostaglandins. | DUKE | | prostaglandin-synthetase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | protisticide | | | DUKE | | tineacide | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | trypanocide | | | 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 | Not Available |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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