| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:21 UTC |
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| Update date | 2019-11-26 03:00:09 UTC |
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| Primary ID | FDB004683 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Obtusifoliol |
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| Description | 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 viability of mammals, essential step in cholesterol biosynthesis; sterol 14-demethylation occurs in all organism exhibiting de novo sterol biosynthesis, and CYP51A1 has been conserved throughout evolution. (PMID: 8797093). Obtusifoliol is found in many foods, some of which are jew's ear, mamey sapote, star fruit, and tinda. |
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| CAS Number | 16910-32-0 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C30H50O |
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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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| 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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| Isomeric SMILES | CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@@H]1CC3 |
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| Average Molecular Weight | 426.7174 |
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| Monoisotopic Molecular Weight | 426.386166222 |
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| Classification |
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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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| GC-MS | Obtusifoliol, 1 TMS, GC-MS Spectrum | splash10-0a5c-4910000000-dad41d67ee45a726de74 | Spectrum | | Predicted GC-MS | Obtusifoliol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Obtusifoliol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-056r-1003900000-3974cb418cf053c4e328 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0560-7139400000-dfd6daa4b47fe2be34cf | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00lr-9187100000-7ee2f7d49200d2ca6ea2 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-e7093af21e32d5894880 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000900000-8428ae6beee69ce08d96 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-3009700000-ae79d303adb71352d425 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-590c9e4adfdd12b64d93 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000900000-da03ad21be78071c2fd8 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00fr-1005900000-ddc6e9faaf47d2ff6736 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-9138200000-b48da05273d106ecd79a | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053r-9211000000-c7a30944f787b77be55c | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001l-9431000000-fc81973855911f7a5782 | 2021-09-23 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 570838 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C01943 |
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| Pubchem Compound ID | 656449 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 17791 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB01242 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | OBTUSIFOLIOL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00007368 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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