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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:37:12 UTC |
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Update Date | 2020-06-04 22:58:00 UTC |
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BMDB ID | BMDB0000827 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Stearic acid |
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Description | Stearic acid, also known as stearate or 18:0, 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. Stearic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Stearic acid exists in all living species, ranging from bacteria to humans. Stearic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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18:0 | ChEBI | Acide octadecanoique | ChEBI | Acide stearique | ChEBI | C18:0 | ChEBI | CH3-[CH2]16-COOH | ChEBI | N-Octadecanoic acid | ChEBI | Octadecansaeure | ChEBI | Octadecoic acid | ChEBI | Oktadekansaeure | ChEBI | Stearinsaeure | ChEBI | Stearate | Kegg | N-Octadecanoate | Generator | Octadecoate | Generator | Octadecanoic acid | HMDB | Octadecanoate | HMDB | 1-Heptadecanecarboxylate | HMDB | 1-Heptadecanecarboxylic acid | HMDB | Stearex beads | HMDB | Stearic acid cherry | HMDB | Stearophanate | HMDB | Stearophanic acid | HMDB | Calcium stearate | HMDB | Aluminum tristearate | HMDB | Ammonium stearate | HMDB | Zinc stearate | HMDB | Magnesium stearate | HMDB | Sodium stearate | HMDB | Aluminum monostearate | HMDB | FA(18:0) | HMDB |
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Chemical Formula | C18H36O2 |
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Average Molecular Weight | 284.4772 |
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Monoisotopic Molecular Weight | 284.271530396 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 57-11-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) |
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InChI Key | QIQXTHQIDYTFRH-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
- Myelin sheath
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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 | 68.8 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.000597 mg/mL | Not Available | LogP | 8.23 | SANGSTER (1993) |
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Predicted Properties | Not Available |
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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
- Myelin sheath
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Biospecimen Locations | - Adipose Tissue
- Blood
- Brain
- Epidermis
- Erythrocyte
- Fibroblasts
- Intestine
- Liver
- Mammary Gland
- Milk
- Muscle
- Neuron
- Oocyte
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Urine
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Pathways | |
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Normal Concentrations |
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Adipose Tissue | Detected and Quantified | 32663.0746 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 27546.67 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 798686.15 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 821695.38 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 299512.0171 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 273535.1 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 | 295489.41 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 322697.21 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 298498.44 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 330184.63 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 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 | Blood | Detected and Quantified | 0.021 +/- 0.011 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Erythrocyte | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | 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 and Quantified | 6.53 +/- 0.12 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6046.18 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 11.5 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4569.79 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1054.566 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1968.523 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1054.566 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 12338.423 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 12197.81 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10897.18 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 13 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 35.90 +/- 5.72 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30.18 +/- 1.56 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 12.36 +/- 1.17 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.78 +/- 0.26 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 24.33 +/- 0.08 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19685.247 +/- 8436.534 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 49.319 +/- 0.34 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 130 +/- 22.8 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 78.2 +/- 9.0 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 | Milk | Detected and Quantified | 12936.0194 +/- 3901.897 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 11846.300 +/- 3655.832 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10194.139 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 84716.807 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 99480.732 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 121626.619 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Neuron | Expected 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 | Platelet | 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 | Ruminal Fluid | Detected and Quantified | 185.6 +/- 27.1 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 186.0 +/- 27.0 uM | Not Specified | Not Specified | Normal | | details | Urine | Detected 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 | HMDB0000827 |
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DrugBank ID | DB03193 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031183 |
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KNApSAcK ID | C00001238 |
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Chemspider ID | 5091 |
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KEGG Compound ID | C01530 |
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BioCyc ID | STEARIC_ACID |
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BiGG ID | 37799 |
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Wikipedia Link | Stearic_acid |
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METLIN ID | 189 |
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PubChem Compound | 5281 |
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PDB ID | Not Available |
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ChEBI ID | 28842 |
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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 | - Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
- 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 ]
- 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 ]
- 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.
- M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
- 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.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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