Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:37 UTC |
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Update date | 2019-11-26 03:08:15 UTC |
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Primary ID | FDB013270 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Tomatidine |
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Description | Tomatidine belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. Based on a literature review a significant number of articles have been published on Tomatidine. |
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CAS Number | 77-59-8 |
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Structure | |
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Synonyms | Synonym | Source |
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(22S,25S)-5alpha-Spirosolan-3beta-ol | HMDB | (3beta,5alpha,22beta,25S)-Spirosolan-3-ol | HMDB | (3beta,5alpha,25S)-Spirosolan-3-ol | HMDB | 5a-Tomatidan-3b-ol, 8ci | HMDB | 5alpha -Tomatidan-3beta -ol | HMDB | 5alpha-Tomatidan-3beta-ol | HMDB | 5alpha-Tomatidan-3beta-ol (8ci) | HMDB | Spirosolan-3-ol | HMDB | Spirosolan-3-ol, (3alpha ,22alpha -tomatidan-3beta -ol | HMDB | Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- (9ci) | HMDB | Tomatidin | HMDB | Soladulcidine | MeSH | Tomatidine, (3beta,5alpha,22alpha,25R)-isomer | MeSH | 5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- Azaspirostan-3 beta-ol | MeSH | (22S,25S)-5alpha-spirosolan-3beta-ol | biospider | (3beta,5alpha,22beta,25S)-spirosolan-3-ol | biospider | (3beta,5alpha,25S)-spirosolan-3-ol | biospider | 5α-Tomatidan-3β-ol | biospider | 5a-Tomatidan-3b-ol, 8CI | db_source | 5alpha-tomatidan-3beta-ol | biospider | 5alpha-Tomatidan-3beta-ol (8CI) | biospider | Spirosolan-3-ol, (3α,22α-Tomatidan-3β-ol | biospider | Spirosolan-3-ol, (3β,5α,22β,25S)- | biospider | Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- | biospider | Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- (9CI) | biospider | Tomatidine | db_source |
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Predicted Properties | |
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Chemical Formula | C27H45NO2 |
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IUPAC name | 5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-16-ol |
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InChI Identifier | InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3 |
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InChI Key | XYNPYHXGMWJBLV-UHFFFAOYSA-N |
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Isomeric SMILES | CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1 |
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Average Molecular Weight | 415.6517 |
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Monoisotopic Molecular Weight | 415.345029689 |
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Classification |
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Description | Belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]Decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']Indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. |
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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 | Steroidal alkaloids |
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Direct Parent | Spirosolanes and derivatives |
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Alternative Parents | |
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Substituents | - Spirosolane skeleton
- 3-hydroxysteroid
- Hydroxysteroid
- Azasteroid
- Azaspirodecane
- Alkaloid or derivatives
- Piperidine
- Tetrahydrofuran
- Cyclic alcohol
- Secondary alcohol
- Hemiaminal
- Organoheterocyclic compound
- Oxacycle
- Secondary amine
- Azacycle
- Secondary aliphatic amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Foods | Fruits and vegetables: |
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Physico-Chemical Properties - Experimental |
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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 78.02%; H 10.91%; N 3.37%; O 7.70% | DFC |
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Melting Point | Mp 210-211° | DFC |
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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 +5 (MeOH) | 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 | Type | Description | Splash Key | View |
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Predicted GC-MS | Tomatidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zg0-1129200000-5d9e624514d0944e171c | Spectrum | Predicted GC-MS | Tomatidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05fr-2215900000-9b8851953955b216ad28 | Spectrum | Predicted GC-MS | Tomatidine, 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 | splash10-014j-0009600000-59abef74949d70a8cafc | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0avj-0198200000-9c90978a91bba76ca55a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-5269000000-c49d77f03cb7c42696cd | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0009600000-59abef74949d70a8cafc | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0avj-0198200000-9c90978a91bba76ca55a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-5269000000-c49d77f03cb7c42696cd | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-0177947b1b0afba7dd49 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0009600000-594f89795c2e81f4b990 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-3119000000-96f892c1d44b480cfcca | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-0177947b1b0afba7dd49 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0009600000-594f89795c2e81f4b990 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-3119000000-96f892c1d44b480cfcca | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0002900000-c098f83c1fc2f2160cf3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-3579800000-be21ff49c8422a55ae65 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-059y-3950000000-8454b0799a2b0fd68bfa | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000900000-713eea1f92e6cf59257a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0001900000-a98be16fc6ee5b3252a6 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03di-0239800000-e6773abcff13370b5fc4 | 2021-09-22 | 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 | C10826 |
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Pubchem Compound ID | 65576 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 9629 |
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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 | HHM52-S:HQO35-K |
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EAFUS ID | Not Available |
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Dr. Duke ID | TOMATIDINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002267 |
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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 | Descriptor | ID | Definition | Reference |
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anti feedant | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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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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