Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:40:21 UTC |
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Updated at | 2021-08-19 23:59:22 UTC |
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NP-MRD ID | NP0002784 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | alpha-Lipoic acid |
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Provided By | BMRB |
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Description | (S)-Lipoic acid, also known as L-6-thioctic acid or (S)-a-lipoate, 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 (S)-Lipoic acid exists in all living organisms, ranging from bacteria to humans. It was first documented in 1951 (PMID: 14854913). Based on a literature review a significant number of articles have been published on (S)-Lipoic acid (PMID: 17984079) (PMID: 10966480) (PMID: 8573188) (PMID: 7669066). |
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Structure | InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1 |
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Synonyms | Value | Source |
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(S)-(-)-Lipoic acid | ChEBI | (S)-1,2-Dithiolane-3-pentanoic acid | ChEBI | (S)-alpha-Lipoic acid | ChEBI | L-1,2-Dithiolane 3-valeric acid | ChEBI | L-6,8-Thioctic acid | ChEBI | L-6-Thioctic acid | ChEBI | LIPOIC ACID | ChEBI | S-LA | ChEBI | SLA | ChEBI | Thioctic acid L-form | ChEBI | (S)-(-)-Lipoate | Generator | (S)-1,2-Dithiolane-3-pentanoate | Generator | (S)-a-Lipoate | Generator | (S)-a-Lipoic acid | Generator | (S)-alpha-Lipoate | Generator | (S)-Α-lipoate | Generator | (S)-Α-lipoic acid | Generator | L-1,2-Dithiolane 3-valerate | Generator | L-6,8-Thioctate | Generator | L-6-Thioctate | Generator | LIPOate | Generator | Thioctate L-form | Generator | (S)-Lipoate | Generator | Acid, alpha-lipoic | HMDB | Thioctic acid | HMDB | alpha Lipoic acid | HMDB | (-)-Thioctic acid | HMDB | (3S)-1,2-Dithiolane-3-pentanoic acid | HMDB | (S)-Thioctic acid | HMDB | S-(-)-alpha-Lipoic acid | HMDB | S-(-)-Α-lipoic acid | HMDB | 1,2-Dithiolane-3-valeric acid | HMDB | 1,2-Dithiolane-3-pentanoic acid | HMDB | 5-(1,2-Dithiolan-3-yl)pentanoic acid | HMDB | 5-(1,2-Dithiolan-3-yl)valeric acid | HMDB | 6,8-Thioctic acid | HMDB | 6-Thioctic acid | HMDB | ALA | HMDB | (S)-Lipoic acid | HMDB |
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Chemical Formula | C8H14O2S2 |
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Average Mass | 206.3260 Da |
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Monoisotopic Mass | 206.04352 Da |
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IUPAC Name | 5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid |
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Traditional Name | S-LA |
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CAS Registry Number | Not Available |
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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-/m0/s1 |
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InChI Key | AGBQKNBQESQNJD-ZETCQYMHSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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 | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. doi: 10.1146/annurev.biochem.69.1.961. [PubMed:10966480 ]
- REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. doi: 10.1126/science.114.2952.93. [PubMed:14854913 ]
- Biewenga GP, Dorstijn MA, Verhagen JV, Haenen GR, Bast A: Reduction of lipoic acid by lipoamide dehydrogenase. Biochem Pharmacol. 1996 Feb 9;51(3):233-8. doi: 10.1016/0006-2952(95)02124-8. [PubMed:8573188 ]
- Loffelhardt S, Bonaventura C, Locher M, Borbe HO, Bisswanger H: Interaction of alpha-lipoic acid enantiomers and homologues with the enzyme components of the mammalian pyruvate dehydrogenase complex. Biochem Pharmacol. 1995 Aug 25;50(5):637-46. doi: 10.1016/0006-2952(95)00175-y. [PubMed:7669066 ]
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