| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:09:46 UTC |
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| Update date | 2019-08-01 18:39:56 UTC |
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| Primary ID | FDB011675 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Palmitoleic acid |
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| Description | Palmitoleic acid, or (Z)-9-hexadecenoic acid, is an omega-7 monounsaturated fatty acid that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues, but generally found in higher concentrations in the liver. It is biosynthesized from palmitic acid by the action of the enzyme delta-9 desaturase. Macadamia oil (Macadamia integrifolia) and Sea Buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40% respectively (Wikipedia). |
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| CAS Number | 373-49-9 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | Not Available |
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| Chemical Formula | C16H30O2 |
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| IUPAC name | |
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| InChI Identifier | InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- |
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| InChI Key | SECPZKHBENQXJG-FPLPWBNLSA-N |
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| Isomeric SMILES | CCCCCC\C=C/CCCCCCCC(O)=O |
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| Average Molecular Weight | 254.4082 |
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| Monoisotopic Molecular Weight | 254.224580204 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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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 | Fatty acids and conjugates |
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| Direct Parent | Long-chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Long-chain 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 - Experimental |
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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 75.54%; H 11.89%; O 12.58% | DFC |
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| Melting Point | Mp 0.5° | DFC |
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| Boiling Point | Bp0.6 162° | DFC |
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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 | Not Available | |
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| Density | Not Available | |
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| Refractive Index | n20D 1.4582 | DFC |
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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 | Not Available |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 393216 |
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| ChEMBL ID | CHEMBL453509 |
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| KEGG Compound ID | C08362 |
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| Pubchem Compound ID | 445638 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 28716 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | DB04257 |
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| HMDB ID | HMDB03229 |
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| CRC / DFC (Dictionary of Food Compounds) ID | CQD88-W:GXX07-I |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | PHYSETOLEIC-ACID|PALMITOLEIC-ACID |
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| BIGG ID | 246167 |
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| KNApSAcK ID | C00029354 |
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| HET ID | PAM |
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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 | Palmitoleic 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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| 5alpha-reductase inhibitor | 50781 | An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone. | DUKE | | soap | | | DUKE |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| S-acyl fatty acid synthase thioesterase, medium chain | OLAH | Q9NV23 |
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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 | 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).
— 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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