Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-09-27 18:34:19 UTC |
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HMDB ID | HMDB0000937 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Stigmasterol |
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Description | Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it (Wikipedia ). Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. |
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Structure | |
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Synonyms | Value | Source |
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(3beta,22E)-Stigmasta-5,22-dien-3-ol | ChEBI | 5,22-Cholestadien-24-ethyl-3beta-ol | ChEBI | beta-Stigmasterol | ChEBI | Phytosterol | ChEBI | Poriferasterol | ChEBI | Stigmasta-5,22-dien-3beta-ol | ChEBI | (3b,22E)-Stigmasta-5,22-dien-3-ol | Generator | (3β,22E)-Stigmasta-5,22-dien-3-ol | Generator | 5,22-Cholestadien-24-ethyl-3b-ol | Generator | 5,22-Cholestadien-24-ethyl-3β-ol | Generator | b-Stigmasterol | Generator | β-Stigmasterol | Generator | Stigmasta-5,22-dien-3b-ol | Generator | Stigmasta-5,22-dien-3β-ol | Generator | (24S)-5,22-Stigmastadien-3b-ol | HMDB | 17-(4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | HMDB | Stigmasta-5,22-dien-3-b-ol | HMDB | Stigmasta-5,22-dien-3-beta-ol | HMDB | Stigmasterin | HMDB | (24S)-24-Ethylcholesta-5,22-dien-3beta-ol | HMDB | (24S)-24-Ethylcholesta-5,22-dien-3β-ol | HMDB | (24S)-5,22-Stigmastadien-3beta-ol | HMDB | (24S)-5,22-Stigmastadien-3β-ol | HMDB | (24S)-Stigmast-5,22-dien-3beta-ol | HMDB | (24S)-Stigmast-5,22-dien-3β-ol | HMDB | 24-Ethyl-5,22-cholestadien-3beta-ol | HMDB | 24-Ethyl-5,22-cholestadien-3β-ol | HMDB | 24beta-Ethyl-5,22-cholestadien-3beta-ol | HMDB | 24β-Ethyl-5,22-cholestadien-3β-ol | HMDB | Stigmasta-5,22(E)-dien-3beta-ol | HMDB | Stigmasta-5,22(E)-dien-3β-ol | HMDB | Stigmasterol | HMDB | delta5,22-Stigmastadien-3beta-ol | HMDB | delta5-Stigmasterol | HMDB | Δ5,22-Stigmastadien-3β-ol | HMDB | Δ5-Stigmasterol | HMDB |
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Chemical Formula | C29H48O |
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Average Molecular Weight | 412.702 |
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Monoisotopic Molecular Weight | 412.370516166 |
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IUPAC Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[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)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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CAS Registry Number | 83-48-7 |
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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)\C=C\[C@@H](CC)C(C)C |
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InChI Identifier | InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 |
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InChI Key | HCXVJBMSMIARIN-PHZDYDNGSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. |
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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 | Stigmastanes and derivatives |
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Direct Parent | Stigmastanes and derivatives |
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Alternative Parents | |
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Substituents | - C24-propyl-sterol-skeleton
- Stigmastane-skeleton
- Triterpenoid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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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 | 170 °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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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-3941000000-4b20188a87c1dadeae49 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a59-9720000000-02211a4df6ec5c313295 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-053r-7941000000-7983b2cb8a74cfda7530 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a59-9731000000-168578ccead65322e450 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-3941000000-4b20188a87c1dadeae49 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a59-9720000000-02211a4df6ec5c313295 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-053r-7941000000-7983b2cb8a74cfda7530 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a59-9731000000-168578ccead65322e450 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001j-1109000000-be897608aaeab74e5d13 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0avl-2102900000-564b610342ad160ee822 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-03di-0000900000-f7738a3fcdee344f82c9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-07cs-9400200000-959314bea26c5acd8301 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0a59-7900000000-ce066e558ecbe29afea8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive | splash10-0a4i-3941000000-f854893a9352ff766734 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-0a59-9720000000-5a3d902c3cd2af078da3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive | splash10-053r-7941000000-6c5c63e8c487f86b353b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive | splash10-0a59-9731000000-32a70fa14fd448314caa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ot-2019500000-3495ed3a1955cc77528a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9128100000-3c3b91bb2d698a88f9db | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-8197000000-a80e8fcc32cd4a2dfefe | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-322cae85ce921a9ef9e2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0004900000-d25be97b0cfa1b9bed79 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000t-2019000000-3b119d03e184f575cdc4 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a59-8920000000-c7d02c3957677fae28be | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Disease References | Sitosterolemia |
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- Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [PubMed:7595097 ]
| Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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General References | - Noblet JA, Young DL, Zeng EY, Ensari S: Use of fecal steroids to infer the sources of fecal indicator bacteria in the Lower Santa Ana River Watershed, California: sewage is unlikely a significant source. Environ Sci Technol. 2004 Nov 15;38(22):6002-8. [PubMed:15573599 ]
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Triana J, Lopez M, Perez FJ, Gonzalez-Platas J, Quintana J, Estevez F, Leon F, Bermejo J: Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities. J Nat Prod. 2005 Apr;68(4):523-31. [PubMed:15844941 ]
- Valsta LM, Lemstrom A, Ovaskainen ML, Lampi AM, Toivo J, Korhonen T, Piironen V: Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake. Br J Nutr. 2004 Oct;92(4):671-8. [PubMed:15522137 ]
- Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. [PubMed:15893885 ]
- Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. [PubMed:10517218 ]
- Miettinen TA: Phytosterolaemia, xanthomatosis and premature atherosclerotic arterial disease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis. Eur J Clin Invest. 1980 Feb;10(1):27-35. [PubMed:6768564 ]
- Urech K, Scher JM, Hostanska K, Becker H: Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L. J Pharm Pharmacol. 2005 Jan;57(1):101-9. [PubMed:15638998 ]
- Morin RJ, Elms NJ: Rapid microanalysis of cholesterol in bile and serum by gas chromatography. Ann Clin Lab Sci. 1975 Jan-Feb;5(1):52-6. [PubMed:1111441 ]
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