| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:21 UTC |
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| Update date | 2019-11-26 03:07:33 UTC |
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| Primary ID | FDB012760 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | (Z,Z)-9,12-Octadecadienoic acid |
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| Description | Constituent of most vegetable oils and animal fats. The Fe salt is the major component of metallic drier compositions used to line food cans
Linoleic acid is one of two essential fatty acids that humans and other animals must ingest for good health, because the body requires them for various biological processes, but cannot synthesize them from other food components. (Z,Z)-9,12-Octadecadienoic acid is found in many foods, some of which are green bean, cloves, kumquat, and pecan nut. |
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| CAS Number | 60-33-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 9E,12Z-Octadecadienoate | Generator | | (9Z,12Z)-9,12-Octadecadienoate | biospider | | (9Z,12Z)-9,12-Octadecadienoic acid | biospider | | (9Z,12Z)-Octadecadienoate | Generator | | (9Z,12Z)-Octadecadienoic acid | biospider | | (Z,Z)-9,12-Octadecadienoate | biospider | | (Z,Z)-9,12-Octadecadienoic acid | biospider | | 9-(Z), 12-(Z)-Octadecadienoic acid | biospider | | 9-cis,12-cis-Linoleate | biospider | | 9-cis,12-cis-Linoleic acid | biospider | | 9-cis,12-cis-Octadecadienoate | biospider | | 9-cis,12-cis-Octadecadienoic acid | biospider | | 9,12-Linoleic acid | biospider | | 9,12-Octadecadienoic acid (Z,Z)- | biospider | | 9Z,12Z-Linoleate | biospider | | 9Z,12Z-Linoleic acid | biospider | | 9Z,12Z-Octadecadienoate | biospider | | 9Z,12Z-Octadecadienoic acid | biospider | | Acide cis-linoleique | ChEBI | | Acide linoleique | ChEBI | | Acido linoleico | ChEBI | | all-cis-9,12-Octadecadienoate | biospider | | all-cis-9,12-Octadecadienoic acid | biospider | | C18:2 9c, 12c Omega6 todos cis-9,12-octadienoico | ChEBI | | C18:2, N-6,9 all-cis | ChEBI | | cis-9-cis-12-Octadecadienoic acid | biospider | | cis-9,cis-12-Octadecadienoate | biospider | | cis-9,cis-12-Octadecadienoic acid | biospider | | cis-D9,12-Octadecadienoate | HMDB | | cis-D9,12-Octadecadienoic acid | HMDB | | cis-delta(9,12)-Octadecadienoate | Generator | | cis-Delta(9,12)-Octadecadienoic acid | ChEBI | | cis-δ(9,12)-octadecadienoate | Generator | | cis-δ(9,12)-octadecadienoic acid | Generator | | cis, cis-9,12-Octadecadienoic acid | biospider | | cis,cis-9,12-Octadecadienoate | Generator | | cis,cis-9,12-octadecadienoic acid | biospider | | Cis,cis-linoleate | biospider | | Cis,cis-linoleic acid | biospider | | Emersol 315 | HMDB | | Extra linoleic 90 | HMDB | | Leinolic acid | db_source | | Linolate | Generator | | Linoleate | Generator | | Linoleic acid | db_source | | Linolic acid | db_source | | Polylin 515 | HMDB | | Telfairic acid | db_source | | Unifac 6550 | HMDB |
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| Predicted Properties | |
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| Chemical Formula | C18H32O2 |
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| IUPAC name | (9E,12Z)-octadeca-9,12-dienoic acid |
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| InChI Identifier | InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9+ |
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| InChI Key | OYHQOLUKZRVURQ-IXWMQOLASA-N |
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| Isomeric SMILES | [H]\C(CCCCC)=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O |
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| Average Molecular Weight | 280.4455 |
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| Monoisotopic Molecular Weight | 280.240230268 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Lineolic acids and derivatives |
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| Direct Parent | Lineolic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Octadecanoid
- Long-chain fatty acid
- Fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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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 | Liquid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 77.09%; H 11.50%; O 11.41% | DFC |
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| Melting Point | Mp -5° | DFC |
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| Boiling Point | Bp0.02 129° | DFC |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | 7.05 | SANGSTER (1993) |
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| Experimental pKa | 4.77 | |
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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 | Not Available | |
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| Density | d254 0.9 | DFC |
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| Refractive Index | n20D 1.4697 | DFC |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | (Z,Z)-9,12-Octadecadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0007-8950000000-f63c2f7a4fb796f5b2d7 | Spectrum |
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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 | splash10-03di-0090000000-8bdf8d54a29f73494242 | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0239-4590000000-fc68aa6b94e255713775 | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rf-9830000000-8617b3536d6af2a7f35f | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-f1e9e4b543f7d4f48bf8 | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ti-0090000000-665523c6142ff4e39c96 | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9240000000-dca36a25ad7519d500c3 | 2018-04-06 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 4444105 |
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| ChEMBL ID | CHEMBL267476 |
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| KEGG Compound ID | C01595 |
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| Pubchem Compound ID | 5280450 |
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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 | HMDB00673 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HDX10-F:HKR32-G |
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| EAFUS ID | 2056 |
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| Dr. Duke ID | LINOLEIC-ACID|OCTADECA-9,12-DIENOIC-ACID |
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| BIGG ID | 37956 |
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| KNApSAcK ID | Not Available |
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| HET ID | EIC |
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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 | rw1045901 |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Linoleic acid |
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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-alpha-reductase inhibitor | 50781 | An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing prostate size, promoting hair growth, and minimizing sebaceous gland activity. | DUKE | | Anti-acne | 50177 | An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin. | DUKE | | Anti-alopecic | 52217 | An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth. | DUKE | | Anti-anaphylactic | 52217 | An agent that prevents or treats anaphylaxis, a severe allergic reaction. It plays a biological role in stabilizing mast cells and reducing histamine release. Therapeutically, it is used to manage allergic emergencies, with key medical applications including treatment of anaphylactic shock, asthma, and allergic rhinitis. | DUKE | | Anti-androgenic | 35497 | An agent that blocks the activity of male sex hormones (androgens), reducing their effects on the body. Therapeutically, it's used to treat conditions like prostate cancer, acne, and hirsutism, as well as manage symptoms of androgen-sensitive disorders, such as benign prostatic hyperplasia. | DUKE | | Anti-arteriosclerotic | 38070 | An agent that prevents or slows the progression of arteriosclerosis, a condition characterized by the hardening and narrowing of arteries. It reduces the formation of plaques, lowering the risk of cardiovascular disease. Therapeutically, it is used to manage atherosclerosis, hyperlipidemia, and hypertension, ultimately reducing the risk of heart attacks and strokes. | DUKE | | Anti-arthritic | 52217 | An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life. | DUKE | | Anti coronary | 52217 | An agent that reduces the risk of coronary artery disease, lowering blood pressure and cholesterol levels. It helps prevent heart attacks, strokes, and other cardiovascular events, commonly used in managing hypertension, hyperlipidemia, and atherosclerosis. | DUKE | | Anti eczemic | 52217 | An agent that reduces inflammation and itching, commonly used to manage eczema symptoms, atopic dermatitis, and other skin allergies, providing relief and preventing flare-ups. | DUKE | | Anti fibrinolytic | | An agent that inhibits the breakdown of blood clots by blocking plasmin formation, used to treat bleeding disorders, such as hemophilia, and to reduce bleeding after surgery or trauma. | DUKE | | Anti-granular | | An agent that inhibits granule formation or release, reducing inflammation and immune responses. Therapeutically, it's used to manage autoimmune disorders, allergic reactions, and inflammatory conditions, such as asthma and rheumatoid arthritis, by suppressing granulocyte activity and cytokine release. | DUKE | | Anti histaminic | 37956 | An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis. | 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 leukotriene-D4 | 35222 | An agent that blocks the action of leukotriene D4, reducing inflammation and bronchoconstriction. Therapeutically, it's used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting leukotriene-mediated responses, providing relief from symptoms such as wheezing, coughing, and shortness of breath. | DUKE | | Anti-menorrhagic | 52217 | An agent that reduces heavy menstrual bleeding, playing a biological role in regulating menstrual flow. Therapeutically, it is used to treat menorrhagia, with key medical applications including managing excessive uterine bleeding, dysmenorrhea, and menstrual disorders. | DUKE | | Anti monosodium-glutamate | | An antidote for MSG poisoning, neutralizing excessive glutamate effects. Biologically, it regulates glutamate levels, mitigating neurotoxicity. Therapeutically, it's used to treat MSG-induced adverse reactions, such as headaches and nausea, and may have applications in managing conditions like migraines and neuropathic pain. | DUKE | | Anti-prostatitic | | An agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome. | 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 | | Carcinogenic | 50903 | An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment. | DUKE | | Comedolytic | | An agent that resolves or prevents comedones (small skin bumps) by unclogging pores, reducing acne formation. Therapeutically, it is used to treat acne, particularly non-inflammatory types, by preventing new comedone formation and promoting skin clarity. Key medical uses include topical treatments for mild to moderate acne. | DUKE | | Hepatoprotective | 62868 | An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities. | DUKE | | Hypocholesterolemic | | An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease. | DUKE | | Immunomodulator | 50846 | An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis. | DUKE | | Insectifuge | 24852 | A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission. | DUKE | | Metastatic | | Refers to the spread of cancer from its primary site to other parts of the body, playing a key role in cancer progression. Therapeutically, understanding metastatic mechanisms informs targeted treatments, such as chemotherapy and radiation therapy, to manage and slow cancer spread, improving patient outcomes. | DUKE | | Nematicide | 25491 | An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health. | DUKE | | Tyrosine kinase inhibitor | | An agent that blocks the enzymatic activity of tyrosine kinases, enzymes responsible for the activation of many proteins involved in signal transduction pathways regulating cell growth and survival. Therapeutically, tyrosine kinase inhibitors are widely used in the treatment of various cancers and proliferative diseases, by halting aberrant signaling that drives tumor progression and pathological tissue remodeling. | DUKE |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Cytochrome P450, family 1, subfamily A, polypeptide 1 | CYP1A1 | A0N0X8 | | Cytochrome P450 2D6 | CYP2D6 | Q6NWU0 | | Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | | Cytosolic acyl coenzyme A thioester hydrolase | ACOT7 | O00154 | | Acyl-coenzyme A thioesterase 2, mitochondrial | ACOT2 | P49753 | | Acyl-coenzyme A thioesterase 4 | ACOT4 | Q8N9L9 | | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | | Acyl-coenzyme A thioesterase 1 | ACOT1 | Q86TX2 |
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| Pathways | | Name | SMPDB Link | KEGG Link |
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| Alpha Linolenic Acid and Linoleic Acid Metabolism | SMP00018 | map00592 |
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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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| faint |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | fatty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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| Files |
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| MSDS | show |
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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 | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— 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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