Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:12 UTC |
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Update date | 2019-11-26 02:59:58 UTC |
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Primary ID | FDB004339 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | alpha-Lipoic acid |
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Description | Lipoate, also known as lipoic acid or 6,8-thioctate, belongs to lipoic acids and derivatives class of compounds. Those are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring. Lipoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lipoate can be synthesized from octanoic acid. Lipoate can also be synthesized into lipoamide and lipoyl-AMP. Lipoate can be found in broccoli and spinach, which makes lipoate a potential biomarker for the consumption of these food products. Lipoate may be a unique E.coli metabolite. Lipoate is a non-carcinogenic (not listed by IARC) potentially toxic compound. |
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CAS Number | 62-46-4 |
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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 | C8H14O2S2 |
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IUPAC name | 5-(1,2-dithiolan-3-yl)pentanoic acid |
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InChI Identifier | InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10) |
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InChI Key | AGBQKNBQESQNJD-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)CCCCC1CCSS1 |
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Average Molecular Weight | 206.326 |
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Monoisotopic Molecular Weight | 206.043521072 |
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Classification |
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Description | Belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Dithiolanes |
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Sub Class | Lipoic acids and derivatives |
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Direct Parent | Lipoic acids and derivatives |
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Alternative Parents | |
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Substituents | - Lipoic_acid_derivative
- Medium-chain fatty acid
- Heterocyclic fatty acid
- Thia fatty acid
- Fatty acyl
- Fatty acid
- 1,2-dithiolane
- Organic disulfide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | Not Available | |
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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 | Not Available | |
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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-Lipoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-4900000000-59fc063b5aa5a8b5db19 | Spectrum | Predicted GC-MS | alpha-Lipoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | alpha-Lipoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | alpha-Lipoic acid, TBDMS_1_1, 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 - 10V, Negative | splash10-00di-0900000000-50da42c94591e9a60c0f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0900000000-1346e3a528dca0514cf7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 90V, Negative | splash10-03di-9000000000-420a38a26d85b4091edb | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 75V, Negative | splash10-03di-9000000000-24b63eebe2fd067ce4b8 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 15V, Negative | splash10-0229-6900000000-44bcc93e18aeabd9ee16 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-03k9-9600000000-4f680dfeae7fa1ece57a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 45V, Negative | splash10-03di-9000000000-6f0b91016a33e202e49b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 60V, Negative | splash10-03di-9000000000-e3d4a7fe022cf20db036 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-0920000000-cf913d1d1afc04e5450c | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bti-5910000000-294c510229247ef63f20 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0bvi-9600000000-f8f54eb79c5d4d5bef48 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0920000000-5a823a30dd1fb434e5b1 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0kmu-1910000000-6f491a68afd82922e71b | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9200000000-330e4766f82ed571497b | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-0970000000-0ae5b11a032d11c1ba6d | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-1900000000-decf255617c1bbd69bfb | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-6900000000-eb58a3d8135ba85d4283 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0190000000-014d2ea36cfae0726a9e | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a59-9500000000-9bbbd7b252fb9a0b438d | 2021-10-12 | 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 | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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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 | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | ALPHA-LIPOIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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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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antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | 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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