| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:32 UTC |
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| Update date | 2019-11-26 02:54:39 UTC |
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| Primary ID | FDB000361 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Nuatigenin |
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| Description | Nuatigenin belongs to furospirostanes and derivatives class of compounds. Those are heterocyclic steroids containing a furospirostane moiety, which a skeleton characterized by the presence of a 1,6-dioxaspiro[4.4]nonane ring system and an androstane moiety. Nuatigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Nuatigenin can be found in oat, which makes nuatigenin a potential biomarker for the consumption of this food product. |
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| CAS Number | 6811-35-4 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C27H42O4 |
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| IUPAC name | 5-(hydroxymethyl)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-en-16'-ol |
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| InChI Identifier | InChI=1S/C27H42O4/c1-16-23-22(30-27(16)12-11-24(2,15-28)31-27)14-21-19-6-5-17-13-18(29)7-9-25(17,3)20(19)8-10-26(21,23)4/h5,16,18-23,28-29H,6-15H2,1-4H3 |
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| InChI Key | NELZMZLNTYWIPD-UHFFFAOYSA-N |
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| Isomeric SMILES | CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)(CO)O1 |
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| Average Molecular Weight | 430.62 |
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| Monoisotopic Molecular Weight | 430.308309832 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as furospirostanes and derivatives. These are heterocyclic steroids containing a furospirostane moiety, which a skeleton characterized by the presence of a 1,6-dioxaspiro[4.4]Nonane ring system and an androstane moiety. |
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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 | Furospirostanes and derivatives |
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| Direct Parent | Furospirostanes and derivatives |
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| Alternative Parents | |
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| Substituents | - Furospirostane-skeleton
- Triterpenoid
- Spirostane skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- Delta-5-steroid
- Ketal
- Cyclic alcohol
- Tetrahydrofuran
- Secondary alcohol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 75.31%; H 9.83%; O 14.86% | DFC |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]20D -86 (c, 0.1 in CHCl3) | DFC |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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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 | splash10-03e9-1032900000-84111627cf1b20d3c6df | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0h9s-3093300000-94c7ea9aa52cc062aa34 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f8a-4094000000-08d1f380575b9f2debf0 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-1011900000-f37ac61ca72822955364 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9013300000-a44d535cf6c4b13d0e5d | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05mn-9047000000-b4f2af1c6199ab098025 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-2c11db7f4225ffd58c75 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000900000-1e829bdbff0dc160825d | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056s-0009400000-1f494a05a85c6d750a03 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-0002900000-e8b77d35d649b3c1d6b4 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-2467900000-82e322db1703e2b64a69 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052b-3941000000-a97077e72ad2497e923b | 2021-10-21 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C04715 |
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| Pubchem Compound ID | 440453 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 15574 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | BBB17-E:BBB17-E |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | NUATIGENIN |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003581 |
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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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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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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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