Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:08 UTC |
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HMDB ID | HMDB0001242 |
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Secondary Accession Numbers | - HMDB0006843
- HMDB01242
- HMDB06843
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Metabolite Identification |
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Common Name | Obtusifoliol |
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Description | Obtusifoliol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, obtusifoliol is considered to be a sterol lipid molecule. Obtusifoliol is found, on average, in the highest concentration within evening primroses. Obtusifoliol has also been detected, but not quantified in, several different foods, such as common chokecherries, jicama, pepper (C. frutescens), avocado, and pecan nuts. This could make obtusifoliol a potential biomarker for the consumption of these foods. Obtusifoliol is an intermediate in the biosynthesis of cholesterol: in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase) (PMID: 9559662 ). CYP51A1 is a housekeeping enzyme essential for the viability of mammals, an essential step in cholesterol biosynthesis. Sterol 14-demethylation occurs in all organisms exhibiting de novo sterol biosynthesis and CYP51A1 has been conserved throughout evolution (PMID: 8797093 ). |
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Structure | [H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h19,21-24,27,31H,3,9-18H2,1-2,4-8H3/t21-,22+,23-,24+,27+,28+,29-,30+/m1/s1 |
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Synonyms | Value | Source |
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4alpha,14alpha-Dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-ol | KEGG | 4alpha,14alpha-Dimethyl-24-methylene-5alpha-cholesta-8-en-3beta-ol | KEGG | 4a,14a-Dimethyl-5a-ergosta-8,24(28)-dien-3b-ol | Generator | 4α,14α-Dimethyl-5α-ergosta-8,24(28)-dien-3β-ol | Generator | 4a,14a-Dimethyl-24-methylene-5a-cholesta-8-en-3b-ol | Generator | 4α,14α-Dimethyl-24-methylene-5α-cholesta-8-en-3β-ol | Generator | (+)-Obtusifoliol | HMDB | (3beta,4alpha,5alpha)-4,14-Dimethylergosta-8,24(28)-dien-3-ol | HMDB | (3β,4α,5α)-4,14-Dimethylergosta-8,24(28)-dien-3-ol | HMDB | 4alpha,14alpha-Dimethyl-delta8,24(28)-ergostadien-3beta-ol | HMDB | 4α,14α-Dimethyl-Δ8,24(28)-ergostadien-3β-ol | HMDB | Obtusifoliol | HMDB |
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Chemical Formula | C30H50O |
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Average Molecular Weight | 426.7174 |
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Monoisotopic Molecular Weight | 426.386166222 |
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IUPAC Name | (2S,5S,6S,7S,11R,14R,15R)-2,6,11,15-tetramethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol |
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Traditional Name | (2S,5S,6S,7S,11R,14R,15R)-2,6,11,15-tetramethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol |
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CAS Registry Number | 16910-32-0 |
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SMILES | [H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C |
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InChI Identifier | InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h19,21-24,27,31H,3,9-18H2,1-2,4-8H3/t21-,22+,23-,24+,27+,28+,29-,30+/m1/s1 |
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InChI Key | MMNYKQIDRZNIKT-VSADUBDNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. |
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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 | Ergostane steroids |
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Direct Parent | Ergosterols and derivatives |
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Alternative Parents | |
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Substituents | - Ergosterol-skeleton
- 14-alpha-methylsteroid
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 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 | - Ergosterols and C24-methyl derivatives (C01943 )
- Ergosterols and C24-methyl derivatives (LMST01030101 )
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Obtusifoliol GC-MS (1 TMS) | splash10-0a5c-4910000000-dad41d67ee45a726de74 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Obtusifoliol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Obtusifoliol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 10V, Positive-QTOF | splash10-056r-1003900000-3974cb418cf053c4e328 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 20V, Positive-QTOF | splash10-0560-7139400000-dfd6daa4b47fe2be34cf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 40V, Positive-QTOF | splash10-00lr-9187100000-7ee2f7d49200d2ca6ea2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 10V, Negative-QTOF | splash10-004i-0000900000-e7093af21e32d5894880 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 20V, Negative-QTOF | splash10-004i-0000900000-8428ae6beee69ce08d96 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 40V, Negative-QTOF | splash10-0a4i-3009700000-ae79d303adb71352d425 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 10V, Negative-QTOF | splash10-004i-0000900000-590c9e4adfdd12b64d93 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 20V, Negative-QTOF | splash10-004i-0000900000-da03ad21be78071c2fd8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 40V, Negative-QTOF | splash10-00fr-1005900000-ddc6e9faaf47d2ff6736 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 10V, Positive-QTOF | splash10-001i-9138200000-b48da05273d106ecd79a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 20V, Positive-QTOF | splash10-053r-9211000000-c7a30944f787b77be55c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Obtusifoliol 40V, Positive-QTOF | splash10-001l-9431000000-fc81973855911f7a5782 | 2021-09-23 | Wishart Lab | View Spectrum |
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