| Record Information |
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| Version | 1.0 |
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| Creation Date | 2018-06-29 22:18:42 UTC |
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| Update Date | 2020-06-04 21:25:57 UTC |
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| BMDB ID | BMDB0062205 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Gadoleic acid |
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| Description | 9Z-Eicosenoic acid, also known as cis-gadoleate or 9C-eicosensaeure, 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. 9Z-Eicosenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (Z)-Eicos-9-enoic acid | ChEBI | | 9C-Eicosensaeure | ChEBI | | C20:1C | ChEBI | | cis-9-Eicosenoic acid | ChEBI | | cis-Delta(9)-Eicosenoic acid | ChEBI | | Eicos-9C-enoic acid | ChEBI | | Eicos-9C-ensaeure | ChEBI | | (Z)-Eicos-9-enoate | Generator | | cis-9-Eicosenoate | Generator | | cis-delta(9)-Eicosenoate | Generator | | cis-Δ(9)-eicosenoate | Generator | | cis-Δ(9)-eicosenoic acid | Generator | | Eicos-9C-enoate | Generator | | 9Z-Eicosenoate | Generator | | Gadoleate | HMDB | | Gadoleic acid | HMDB | | FA(20:1(9Z)) | HMDB | | cis-Gadoleate | HMDB |
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| Chemical Formula | C20H38O2 |
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| Average Molecular Weight | 310.522 |
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| Monoisotopic Molecular Weight | 310.287180464 |
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| IUPAC Name | (9Z)-icos-9-enoic acid |
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| Traditional Name | gadoleic acid |
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| CAS Registry Number | 29204-02-2 |
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| SMILES | [H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(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/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11- |
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| InChI Key | LQJBNNIYVWPHFW-QXMHVHEDSA-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 | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
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| Physical Properties |
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| State | Not Available |
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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 | | Spectrum Type | Description | Splash Key | |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-9770000000-8bafce752dcc0e83c211 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00vi-9561000000-84617bccb2d2f0e64718 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-0197000000-f6093bc2d61dbe668e18 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxu-3591000000-835bb134b9d517428e95 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0007-8960000000-fa7ac5e35243596e982c | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0029000000-053d5a3b1d592fd190c2 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1079000000-323c653227521538a43c | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9230000000-33c06ae5cc68dad15291 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-4297000000-a679e8ed0942db48f672 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06r6-9572000000-31bd41e72217aeb75998 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9100000000-e4e0ee937a9dc02d22a0 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0019000000-0d96115f81e42756fc2f | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1069000000-e54a7d130deccefa86bb | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9020000000-c097ab1d18e1ea28f2f1 | View in MoNA |
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| Biological Properties |
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| Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
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| Biospecimen Locations | - Adipose Tissue
- Milk
- Muscle
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 3692.94 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 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 | 2608.51 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1449.17 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1777.65 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 598.99 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 169.78 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 158.83 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1829.24 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 2646.48 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 3707.98 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 96.612 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 96.612 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 96.612 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 1255.95 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected 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 | HMDB0062436 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB003771 |
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| KNApSAcK ID | C00053190 |
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| Chemspider ID | 4445894 |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Gadoleic acid |
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| METLIN ID | Not Available |
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| PubChem Compound | 5282767 |
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| PDB ID | Not Available |
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| ChEBI ID | 32419 |
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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 | - 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 ]
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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