Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:13 UTC |
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Update Date | 2020-06-04 22:59:16 UTC |
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BMDB ID | BMDB0000067 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cholesterol |
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Description | Cholesterol, also known as cholesterin or cordulan, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholesterol is considered to be a sterol lipid molecule. Cholesterol 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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(3beta,14beta,17alpha)-Cholest-5-en-3-ol | ChEBI | Cholest-5-en-3beta-ol | ChEBI | Cholesterin | ChEBI | (3b,14b,17a)-Cholest-5-en-3-ol | Generator | (3Β,14β,17α)-cholest-5-en-3-ol | Generator | Cholest-5-en-3b-ol | Generator | Cholest-5-en-3β-ol | Generator | (3Β)-cholest-5-en-3-ol | HMDB | (3beta)-Cholest-5-en-3-ol | HMDB | 3Β-hydroxycholest-5-ene | HMDB | 3beta-Hydroxycholest-5-ene | HMDB | 5:6-Cholesten-3β-ol | HMDB | 5:6-Cholesten-3beta-ol | HMDB | (-)-Cholesterol | HMDB | Cholesterine | HMDB | Cholesterol base H | HMDB | Cholesteryl alcohol | HMDB | Cholestrin | HMDB | Cholestrol | HMDB | Cordulan | HMDB | Dastar | HMDB | Dusoline | HMDB | Dusoran | HMDB | Dythol | HMDB | Fancol CH | HMDB | Hydrocerin | HMDB | Kathro | HMDB | Lanol | HMDB | Super hartolan | HMDB | Tegolan | HMDB | Cholesterol | HMDB | delta5-Cholesten-3beta-ol | PhytoBank | Δ5-Cholesten-3β-ol | PhytoBank |
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Chemical Formula | C27H46O |
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Average Molecular Weight | 386.6535 |
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Monoisotopic Molecular Weight | 386.354866094 |
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IUPAC Name | (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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Traditional Name | (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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CAS Registry Number | 57-88-5 |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C |
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InChI Identifier | InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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InChI Key | HVYWMOMLDIMFJA-DPAQBDIFSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol-skeleton
- Cholesterol
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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 | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Golgi
- Lysosome
- Membrane
- Mitochondria
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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 | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-004i-3911000000-52f5261007adc218f8f8 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052b-2932000000-1667c83d002043a59fff | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000l-9527000000-5529a262047f5369c9c1 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0mkr-2954000000-60e7d1f5973e4de33dec | View in MoNA |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-014i-1009000000-e82b8e23dedb45ce70e6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-056v-2900000000-04687c9f19ff52ba4654 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05i3-1109000000-8cd386b595bd5151c5a2 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0006-3104900000-698223f49da0b0c1cf81 | 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 GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 27V, positive | splash10-052u-0690000000-36b4aea6637bdf069b5d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 5V, positive | splash10-014i-3639000000-18a9275beb9bae48c1d7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 10V, positive | splash10-014j-4934000000-f755ada933cfcf53c303 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 15V, positive | splash10-0002-5921000000-e7d43c825b9f6d45e679 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 20V, positive | splash10-0532-5910000000-ce90c49b7429a03a65da | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 30V, positive | splash10-05nb-8900000000-2e8913fec7126b5b2a62 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 40V, positive | splash10-0apl-9600000000-3096c7a78c3dd2e6a538 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 50V, positive | splash10-067l-9400000000-1b57543b4cd0a05b9b3f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - QTOF 60V, positive | splash10-0aru-9300000000-45a29b76dfefce3f01ca | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0009000000-dccd68f70545aeac4fab | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05p9-3149000000-7f25daf2b709c7e0d177 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0c00-6269000000-5333d0216e01a3e43367 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-dc853b29b9e884bbb03b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0009000000-09d9608700564a6fef78 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ldi-1009000000-96f6e67651380e1c959e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-2d9cbc8b5b1fa392fb9b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0abj-9173000000-9086873e4b65db1ced63 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-8920000000-bd94fa538afb75d04765 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-c037f2d2f217e99b79ac | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0009000000-7de5154056e69e7319e1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-0009000000-96c53273291d4857bde4 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Not Available | View in JSpectraViewer |
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All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 3341.493 +/- 370.616 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 3290 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 775.888 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 5560534.173 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 4189797.842 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 4138071.943 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 5431219.425 uM | Not Specified | Not Specified | Normal | | details | Blood | 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 and Quantified | 129.315 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 362.0813 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 103.452 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 103.452 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 129.315 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 155.178 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 155.178 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 362.0813 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 206.904 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 206.904 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 206.904 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 206.904 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 206.904 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 77.589 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 89.744 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 77.589 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 258.629 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 258.629 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 362.0813 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 362.0813 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 362.0813 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 362.0813 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 101.383 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 51.726 uM | 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 | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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General References | - Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21. [PubMed:16859856 ]
- 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 ]
- 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.
- USDA Food Composition Databases [Link]
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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