| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:53:14 UTC |
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| Update Date | 2020-06-04 22:40:23 UTC |
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| BMDB ID | BMDB0002259 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Heptadecanoic acid |
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| Description | Heptadecanoic acid, also known as 17:0 or heptadecoate, 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. Heptadecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Heptadecanoic acid exists in all living species, ranging from bacteria to humans. In cattle, heptadecanoic acid is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(8:0/17:0/17:0) pathway. Heptadecanoic acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 17:0 | ChEBI | | C17:0 | ChEBI | | CH3-[CH2]15-COOH | ChEBI | | Heptadecoic acid | ChEBI | | Heptadecylic acid | ChEBI | | Margaric acid | ChEBI | | Margarinic acid | ChEBI | | Margarinsaeure | ChEBI | | N-Heptadecanoic acid | ChEBI | | N-Heptadecoic acid | ChEBI | | N-Heptadecylic acid | ChEBI | | Heptadecoate | Generator | | Heptadecylate | Generator | | Margarate | Generator | | Margarinate | Generator | | N-Heptadecanoate | Generator | | N-Heptadecoate | Generator | | N-Heptadecylate | Generator | | Heptadecanoate | Generator | | Margaric acid, potassium salt | MeSH | | Margaric acid, sodium salt | MeSH | | Omega I-123 heptadecanoic acid | MeSH | | Margaric acid, 1-(11)C-labeled | MeSH | | Margaric acid, nickel (2+) salt | MeSH | | Margaroate | HMDB | | Margaroic acid | HMDB | | Normal-heptadecanoate | HMDB | | Normal-heptadecanoic acid | HMDB | | FA(17:0) | HMDB | | Heptadecanoic acid | MeSH |
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| Chemical Formula | C17H34O2 |
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| Average Molecular Weight | 270.4507 |
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| Monoisotopic Molecular Weight | 270.255880332 |
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| IUPAC Name | heptadecanoic acid |
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| Traditional Name | heptadecanoic acid |
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| CAS Registry Number | 506-12-7 |
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| SMILES | CCCCCCCCCCCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19) |
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| InChI Key | KEMQGTRYUADPNZ-UHFFFAOYSA-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
- 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 | 61.3 °C | 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
- Blood
- Liver
- Mammary Gland
- Milk
- Muscle
- Oocyte
- Placenta
- Prostate Tissue
- Skeletal Muscle
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 1388.9 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1560.21 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 and Quantified | 29403.81 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 40514.59 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 18339.46 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 22412 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 | 33943.34 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 37271.12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 33677.12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 37481.88 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | 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 | | 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 and Quantified | 5176.544 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5916.0505 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 6655.557 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7025.31 uM | 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 | | Muscle | 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 | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details |
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| External Links |
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| HMDB ID | HMDB0002259 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB004676 |
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| KNApSAcK ID | C00007426 |
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| Chemspider ID | 10033 |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | CPD-7830 |
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| BiGG ID | 215873 |
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| Wikipedia Link | Heptadecanoic_acid |
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| METLIN ID | 6578 |
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| PubChem Compound | 10465 |
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| PDB ID | Not Available |
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| ChEBI ID | 32365 |
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| References |
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| Synthesis Reference | Heiduschka, A.; Ripper, J. Heptadecylic acid. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 56B 1736-9. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- 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 ]
- Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
- GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
- Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
- Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
- M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
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