| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:52:58 UTC |
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| Update Date | 2020-06-04 21:52:01 UTC |
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| BMDB ID | BMDB0002231 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Eicosenoic acid |
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| Description | 11Z-Eicosenoic acid, also known as 11-eicosenoate or cis-gondoic acid, 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. Based on a literature review a significant number of articles have been published on 11Z-Eicosenoic acid. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (11Z)-Eicosenoic acid | ChEBI | | (11Z)-Icosenoic acid | ChEBI | | (Z)-Eicos-11-enoic acid | ChEBI | | (Z)-Icos-11-enoic acid | ChEBI | | (Z)-Icosa-11-enoic acid | ChEBI | | 11-Eicosenoic acid | ChEBI | | 11-Icosenoic acid | ChEBI | | 20:1 | ChEBI | | cis-11-Eicosenoic acid | ChEBI | | cis-Delta(11)-Eicosenoic acid | ChEBI | | cis-Gondoic acid | ChEBI | | Eicosenoic acid | ChEBI | | Gondoic acid | ChEBI | | Z-Delta(11)-Eicosensaeure | ChEBI | | (11Z)-Eicosenoate | Generator | | (11Z)-Icosenoate | Generator | | (Z)-Eicos-11-enoate | Generator | | (Z)-Icos-11-enoate | Generator | | (Z)-Icosa-11-enoate | Generator | | 11-Eicosenoate | Generator | | 11-Icosenoate | Generator | | cis-11-Eicosenoate | Generator | | cis-delta(11)-Eicosenoate | Generator | | cis-Δ(11)-eicosenoate | Generator | | cis-Δ(11)-eicosenoic acid | Generator | | cis-Gondoate | Generator | | Eicosenoate | Generator | | Gondoate | Generator | | Z-Δ(11)-eicosensaeure | Generator | | 11Z-Eicosenoate | Generator | | (11Z)-Icos-11-enoate | HMDB | | (11Z)-Icos-11-enoic acid | HMDB | | 11(Z)-Eicosenoate | HMDB | | 11(Z)-Eicosenoic acid | HMDB | | 11-cis-Eicosenoate | HMDB | | 11-cis-Eicosenoic acid | HMDB | | 11Z-Eicosenoic acid | HMDB | | 20:1(N-9) | HMDB | | 20:1n9 | HMDB | | cis-11-Icosenoate | HMDB | | cis-11-Icosenoic acid | HMDB | | FA(20:1(11Z)) | HMDB | | FA(20:1n9) | HMDB | | (11Z)-11-Eicosenoic acid | PhytoBank | | (Z)-11-Eicosenoic acid | PhytoBank | | cis-delta11-Eicosenoic acid | PhytoBank | | cis-Δ11-Eicosenoic acid | PhytoBank |
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| Chemical Formula | C20H38O2 |
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| Average Molecular Weight | 310.5145 |
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| Monoisotopic Molecular Weight | 310.28718046 |
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| IUPAC Name | (11Z)-icos-11-enoic acid |
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| Traditional Name | cis-11-eicosenoic acid |
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| CAS Registry Number | 26764-41-0 |
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| SMILES | CCCCCCCC\C=C/CCCCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9- |
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| InChI Key | BITHHVVYSMSWAG-KTKRTIGZSA-N |
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| Chemical Taxonomy |
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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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Biospecimen Locations | - Adipose Tissue
- Erythrocyte
- Liver
- Mammary Gland
- Milk
- Oocyte
- Placenta
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 254.67 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 282.37 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 2743.93 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 3234.66 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 4849.0167 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 5011.97 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 9274.93 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 7825.72 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 9184.76 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 7787.076 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Erythrocyte | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Oocyte | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0002231 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB012569 |
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| KNApSAcK ID | C00035628 |
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| Chemspider ID | 4445895 |
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| KEGG Compound ID | C16526 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Eicosenoic acid |
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| METLIN ID | 6563 |
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| PubChem Compound | 5282768 |
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| PDB ID | Not Available |
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| ChEBI ID | 32425 |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
- Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.
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