Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2017-12-07 02:44:39 UTC |
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HMDB ID | HMDB0014312 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (S)-lipoic acid |
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Description | Lipoic acid (LA), also known as ?-lipoic acid[2] and alpha lipoic acid (ALA)[3] is an organosulfur compound derived from octanoic acid. The carbon atom at C6 is chiral and the molecule exists as two enantiomers (R)-(+)-lipoic acid (RLA) and (S)-(-)-lipoic acid (SLA) and as a racemic mixture (R/S)-lipoic acid (R/S-LA). Only the (R)-(+)-enantiomer exists in nature and is an essential cofactor of four mitochondrial enzyme complexes. Endogenously synthesized RLA is essential for life and aerobic metabolism. The precursor to lipoic acid, octanoic acid, is made via fatty acid biosynthesis in the form of octanoyl-acyl carrier protein. In eukaryotes, a second fatty acid biosynthetic pathway in mitochondria is used for this purpose. The octanoate is transferred from a thioester of acyl carrier protein to an amide of the lipoyl domain by an octanoyltransferase. The sulfur centers are inserted into the 6th and 8th carbons of octanoate via a radical SAM mechanism, by lipoyl synthase. Lipoic acid can be removed whenever proteins are degraded and by action of the enzyme lipoamidase.[8] Free lipoate can be attached to the lipoyl domain by the enzyme lipoate protein ligase. The ligase activity of this enzyme requires ATP. Lipoate protein ligases proceed via an enzyme bound lipoyl adenylate intermediate. Both RLA and R/S-LA are available as over-the-counter nutritional supplements and have been used nutritionally and clinically since the 1950s for various diseases and conditions. It is often regarded as a vitamin-like antioxidant. Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity. |
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Structure | |
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Synonyms | Value | Source |
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(+)-alpha-Lipoic acid | ChEBI | (R)-(+)-Lipoate | ChEBI | (R)-(+)-Lipoic acid | ChEBI | (R)-1,2-Dithiolane-3-pentanoic acid | ChEBI | (R)-1,2-Dithiolane-3-valeric acid | ChEBI | (R)-6,8-Thioctic acid | ChEBI | alpha-Lipoic acid | ChEBI | Lipoic acid | ChEBI | R-(+)-Lipoic acid | ChEBI | R-LA | ChEBI | RLA | ChEBI | Thioctic acid | ChEBI | Thioctic acid D-form | ChEBI | (+)-a-Lipoate | Generator | (+)-a-Lipoic acid | Generator | (+)-alpha-Lipoate | Generator | (+)-α-lipoate | Generator | (+)-α-lipoic acid | Generator | (R)-Lipoate | Generator | (R)-1,2-Dithiolane-3-pentanoate | Generator | (R)-1,2-Dithiolane-3-valerate | Generator | (R)-6,8-Thioctate | Generator | a-Lipoate | Generator | a-Lipoic acid | Generator | alpha-Lipoate | Generator | α-lipoate | Generator | α-lipoic acid | Generator | Lipoate | Generator | R-(+)-Lipoate | Generator | Thioctate | Generator | Thioctate D-form | Generator | Alpha Lippon al | MeSH | Alpha-Lippon al | MeSH | AlphaLippon al | MeSH | Alphaflam | MeSH | Hexal brand OF thioctic acid | MeSH | Injekt, thiogamma | MeSH | Liponsaure ratiopharm | MeSH | Liponsaure-ratiopharm | MeSH | Stadapharm brand OF thioctic acid | MeSH | Thioctacide T | MeSH | Verla lipon | MeSH | Viatris brand OF thioctic acid | MeSH | alpha Liponaure heumann | MeSH | alpha Liponsaure von CT | MeSH | AlphaLiponsaure von CT | MeSH | Duralipon | MeSH | Ratiopharm brand OF thioctic acid | MeSH | Aliud brand OF thioctic acid | MeSH | Alpha-Liponsaure sofotec | MeSH | AlphaLipon stada | MeSH | Azulipont | MeSH | Heumann brand OF thioctic acid | MeSH | Illa brand OF thioctic acid | MeSH | Illa brand OF thioctic acid tromethamine | MeSH | Juta brand OF thioctic acid | MeSH | MTW Alphaliponsaure | MeSH | Pleomix Alpha | MeSH | PleomixAlpha | MeSH | PleomixAlpha N | MeSH | Q Pharm brand OF thioctic acid | MeSH | Q-Pharm brand OF thioctic acid | MeSH | Thiogamma injekt | MeSH | alpha Vibolex | MeSH | AlphaVibolex | MeSH | biomo Brand OF thioctic acid | MeSH | biomo-Lipon | MeSH | Biomolipon | MeSH | CT-Arzneimittel brand OF thioctic acid | MeSH | Acid, alpha-lipoic | MeSH | Alpha Lipogamma | MeSH | Alpha Lipon stada | MeSH | Alpha-Lipogamma | MeSH | Alpha-Lipon stada | MeSH | AlphaLipogamma | MeSH | AlphaLiponsaure sofotec | MeSH | Fenint | MeSH | Juthiac | MeSH | Merck dura brand OF thioctic acid | MeSH | Pleomix Alpha N | MeSH | Rosen brand OF thioctic acid | MeSH | Thiogamma oral | MeSH | Tromlipon | MeSH | Trommsdorgg brand OF thioctic acid | MeSH | Viatris brand OF thioctic acid tromethamine | MeSH | Worwag brand OF thioctic acid | MeSH | Worwag brand OF thioctic acid meglumine | MeSH | alpha Lipoic acid | MeSH | alpha-Liponsaure von CT | MeSH | alpha-Vibolex | MeSH | AlphaLiponaure heumann | MeSH | biomo Lipon | MeSH | CT Arzneimittel brand OF thioctic acid | MeSH | Esparma brand OF thioctic acid | MeSH | Alpha Liponsaure sofotec | MeSH | Azupharma brand OF thioctic acid | MeSH | Generosan brand OF thioctic acid | MeSH | Lichtenstein brand OF thioctic acid | MeSH | Liponsaureratiopharm | MeSH | MTW Brand OF thioctic acid | MeSH | MTW-Alphaliponsaure | MeSH | MTWAlphaliponsaure | MeSH | Neurium | MeSH | Pharmacia brand OF thioctic acid | MeSH | Pleomix-Alpha | MeSH | Pleomix-Alpha N | MeSH | Sofotec brand OF thioctic acid | MeSH | Thioctacid | MeSH | Verla brand OF thioctic acid | MeSH | Verla-lipon | MeSH | VerlaLipon | MeSH | alpha-Liponaure heumann | MeSH | Espa lipon | MeSH | Espa-lipon | MeSH | Espalipon | MeSH |
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Chemical Formula | C8H14O2S2 |
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Average Molecular Weight | 206.326 |
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Monoisotopic Molecular Weight | 206.043521072 |
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IUPAC Name | 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid |
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Traditional Name | lipoic acid |
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CAS Registry Number | 1077-27-6 |
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SMILES | OC(=O)CCCC[C@@H]1CCSS1 |
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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)/t7-/m1/s1 |
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InChI Key | AGBQKNBQESQNJD-SSDOTTSWSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as lipoic acids and derivatives. These 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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Disposition | Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.22 g/L | Not Available | LogP | 2.1 | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0aba-3900000000-46fc1d57abcc26f6720e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ufu-5900000000-716655e029db4b97efd9 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0hbi-6920000000-011fb15a0f9ca4513029 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4r-0940000000-dead1b29e79e0002da2a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0f8c-9200000000-b6035bdb4abd0d267297 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0059-9000000000-62e73cabbac1531f5145 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-1920000000-2b265e3ed116fbc0a2ea | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ab9-2910000000-9142e84d978f4a481551 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9200000000-8bdfe1c35977a8c80985 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-0940000000-6cecd351951f396a3035 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08gr-6910000000-f169816d57d2290b0d9e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0m2c-9700000000-57ae386a681b98208a4b | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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