Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:59 UTC |
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Update date | 2019-11-26 03:09:20 UTC |
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Primary ID | FDB013944 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Solasodine |
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Description | Solasodine, also known as tomatidenol, 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 Solasodine. |
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CAS Number | 126-17-0 |
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Structure | |
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Synonyms | Synonym | Source |
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Solasodine citrate, (3alpha,22alpha,25R)-isomer | MeSH | Solasodine, (3beta,22beta,25S)-isomer | MeSH | Tomatidenol | MeSH | Purapuridine | HMDB | Salasdine | HMDB | Salasodine | HMDB | Solancarpidine | HMDB | Solancarpine | HMDB | Solanidine S | HMDB | Solanidine-S | HMDB | Solasod-5-en-3 beta-ol | HMDB | Solasod-5-en-3beta -ol | HMDB | Solasodin | HMDB | Solasodine hydrochloride base | HMDB | Sosasodine | HMDB | Spirosol-5-en-3-ol | HMDB | Solasodine | MeSH | Solanidine-s | biospider | Solasod-5-en-3α,25R)- | biospider | Solasod-5-en-3β-ol | biospider | Spirosol-5-en-3-ol, (3β,22α,25R)- | biospider |
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Predicted Properties | |
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Chemical Formula | C27H43NO2 |
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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'-piperidin]-18-en-16-ol |
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InChI Identifier | InChI=1S/C27H43NO2/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/h5,16-17,19-24,28-29H,6-15H2,1-4H3 |
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InChI Key | KWVISVAMQJWJSZ-UHFFFAOYSA-N |
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Isomeric SMILES | CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1 |
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Average Molecular Weight | 413.6358 |
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Monoisotopic Molecular Weight | 413.329379625 |
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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-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- Azasteroid
- Delta-5-steroid
- Azaspirodecane
- Alkaloid or derivatives
- Piperidine
- Cyclic alcohol
- Tetrahydrofuran
- Hemiaminal
- Secondary alcohol
- Oxacycle
- Azacycle
- Secondary aliphatic amine
- Organoheterocyclic compound
- Secondary amine
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Alcohol
- Amine
- Organonitrogen compound
- Organooxygen compound
- 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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Ontology | No ontology term |
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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 78.40%; H 10.48%; N 3.39%; O 7.74% | DFC |
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Melting Point | Mp 200-201° | 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]D -98 (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 | alpha-Solanigrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000w-0129000000-c0f006faa45f6504b94a | Spectrum | Predicted GC-MS | alpha-Solanigrine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-2116900000-ffdb43be61543b5cdf31 | Spectrum | Predicted GC-MS | alpha-Solanigrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | alpha-Solanigrine, 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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MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0000900000-e0308c250bfeb4a8e3f0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0100900000-885f5ba1460df2a81f9d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0a4j-0910000000-83c702d144b914031b01 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ot-0009500000-894bee60ed0946470ec4 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0w91-0198200000-bd353c3bcebbb6b18195 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0mpp-4298000000-ff41d9eaa787776766c6 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-556f3f408a422b05cd8c | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dl-0009600000-00a27d38d42e4d209801 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-3119000000-6c61de8babead29f83fb | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ot-0009500000-894bee60ed0946470ec4 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0w91-0198200000-bd353c3bcebbb6b18195 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0mpp-4298000000-ff41d9eaa787776766c6 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-556f3f408a422b05cd8c | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dl-0009600000-00a27d38d42e4d209801 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-3119000000-6c61de8babead29f83fb | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0002900000-0a90221781aebad0d4ad | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dj-1377900000-c3848916e815c4aa8126 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006w-2941000000-15316ff6e3dbd8eff7a1 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000900000-c711d723aed1a4c0a919 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0001900000-d4db0d16b12f8c57b0f6 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03di-0029400000-17c2461a5822bb81c1e7 | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 5060 |
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ChEMBL ID | CHEMBL1964743 |
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KEGG Compound ID | C10822 |
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Pubchem Compound ID | 5250 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 565242 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35282 |
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CRC / DFC (Dictionary of Food Compounds) ID | HKH07-E:JKY38-R |
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EAFUS ID | Not Available |
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Dr. Duke ID | SOLASODINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002264 |
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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 | Solasodine |
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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 androgenic | 35497 | A compound which inhibits or antagonises the biosynthesis or actions of androgens. | DUKE | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti carcinomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti cholinesterase | 37733 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). | DUKE | anti fertility | | | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti melanomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti spermatogenic | | | DUKE | anti tachycardic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | contraceptive | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | embryotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hepatomegalic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | 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 | teratogenic | 50905 | A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. | 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).
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