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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MCDB 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 belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound. |
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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 | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 57-88-5 |
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SMILES | Not Available |
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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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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 | Not Available |
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Spectra |
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Concentrations |
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Detected and Quantified | 101 uM | | | details | Detected and Quantified | 362 uM | | | details | Detected but not Quantified | Not Applicable | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 129 uM | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 362 uM | | | details | Detected and Quantified | 103 uM | | | details | Detected and Quantified | 103 uM | | | details | Detected and Quantified | 129 uM | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 52 uM | | | details | Detected and Quantified | 155 uM | | | details | Detected and Quantified | 155 uM | | | details | Detected and Quantified | 362 uM | | | details | Detected and Quantified | 206 uM | | | details | Detected and Quantified | 206 uM | | | details | Detected and Quantified | 206 uM | | | details | Detected and Quantified | 206 uM | | | details | Detected and Quantified | 206 uM | | | details | Detected and Quantified | 78 uM | | | details | Detected and Quantified | 90 uM | | | details | Detected and Quantified | 78 uM | | | details | Detected and Quantified | 258 uM | | | details | Detected and Quantified | 258 uM | | | details | Detected and Quantified | 362 uM | | | details | Detected and Quantified | 362 uM | | | details | Detected and Quantified | 362 uM | | | details | Detected but not Quantified | Not Applicable | | | details |
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External Links |
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HMDB ID | HMDB0000067 |
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DrugBank ID | DB04540 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB013269 |
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KNApSAcK ID | C00003648 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C00187 |
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BioCyc ID | CHOLESTEROL |
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BiGG ID | Not Available |
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Wikipedia Link | Cholesterol |
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METLIN ID | Not Available |
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PubChem Compound | 5997 |
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PDB ID | Not Available |
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ChEBI ID | 16113 |
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References |
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Synthesis Reference | Zhu, Yongming; Qin, Liena; Liu, Rui. Simple method for synthesis cholesterol from Diosgenin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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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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