Lipoic acid
PubChem CID: 6112
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| Compound Synonyms | lipoic acid, 1200-22-2, (R)-lipoic acid, (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid, (R)-(+)-1,2-Dithiolane-3-pentanoic acid, (R)-alpha-Lipoic acid, (+)-alpha-Lipoic acid, 1,2-Dithiolane-3-pentanoic acid, (3R)-, R-alpha-Lipoic acid, Thioctic acid d-form, D-Thioctic acid, R-(+)-Thioctic acid, Berlition, Thiogamma, Lipoec, Tiobec, (R)-1,2-Dithiolane-3-pentanoic acid, 5-[(3R)-dithiolan-3-yl]pentanoic acid, R-Lipoic acid, (R)-(+)-lipoic acid, (R)-6,8-thioctic acid, (R)-1,2-Dithiolane-3-valeric Acid, 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid, (R)-(+)-Lipoate, alpha-(+)-Lipoic acid, 1,2-Dithiolane-3R-pentanoic acid, (R)-(+)-a-Lipoic acid, MFCD01631142, (r)-(+)-alpha-lipoic acid, R-(+)-Lipoic acid, Lipoic acid (Standard), R-LA, VLL71EBS9Z, (3R)-1,2-Dithiolane-3-pentanoic Acid, R-(+)-alpha-Lipoic acid, CHEMBL134342, Heparlipon, CHEBI:30314, C8H14O2S2, Thioderm, Tiobec Retard, R-Lipoate, Byodinoral 300, UNII-VLL71EBS9Z, Thioctanoic acid, (+)-thioctic acid, (R)-Thioctic Acid, R-alpha Lipoic acid, ARLIPOIC ACID, Thioctic acid, d form, (y)-alpha-Lipoic Acid, 1,2-Dithiolane-3-pentanoic acid, (R)-, (+)-, A-Lipoic acid, (?)-alpha-Lipoic Acid, (R)-5-(1,2-Dithiolan-3-yl)pentanoicacid, SCHEMBL7924, (+)- alpha -Lipoic acid, ARLIPOIC ACID [INN], Lopac0_001129, (R)-(+)-?-Lipoic Acid, (R)-(+)-, A-Lipoic Acid, GTPL4822, DTXSID20152651, D-THIOCTIC ACID [WHO-DD], .ALPHA.-LIPOIC ACID, D-, GLXC-03742, HMS3263B19, THIOCTIC ACID D-FORM [MI], Tox21_501129, BDBM50106731, HY-18733R, LMFA01130001, s3998, (+)-1,2-Dithiolane-3-valeric Acid, (R)-6,8-DITHIOOCTANOIC ACID, AKOS015892879, AC-8133, CCG-205204, CS-5076, DB00166, FL24904, LP01129, SDCCGSBI-0051097.P002, NCGC00094396-01, NCGC00094396-02, NCGC00094396-03, NCGC00094396-04, NCGC00094396-05, NCGC00094396-06, NCGC00261814-01, AC-11124, AS-11009, HY-18733, ( inverted question mark)-alpha-Lipoic Acid, CS-0694941, EU-0101129, L0207, NS00068623, (R)-(+)--Lipoic acid, R-(+)-Thioctic acid, T 5625, (R)-(+)-alpha-Lipoic acid, analytical standard, EN300-7352963, SR-01000076163, (R)-(+)-1,2-Dithiolane-3-pentanoic acid, 97%, (R)-(+)-alpha-Lipoic acid, >=98.0% (HPLC), SR-01000076163-1, Q27887203, Z1269228108, ( inverted question mark)-1,2-Dithiolane-3-pentanoic acid, R-(+)-alpha-Lipoic acid, (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid, (3R)-1,2-Dithiolane-3-pentanoic acid, (R)-(+)-1,2-Dithiolane-3-pentanoic acid, (+)-1,2-Dithiolane-3-valeric acid |
|---|---|
| Topological Polar Surface Area | 87.9 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 12.0 |
| Description | A vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 150.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 1.0 |
| Enzyme Uniprot Id | Q9Y234 |
| Uniprot Id | O00330, P10515, P16435, P36957, P23434, P11182, Q9NWU1, Q9Y234 |
| Iupac Name | 5-[(3R)-dithiolan-3-yl]pentanoic acid |
| Prediction Hob | 1.0 |
| Class | Dithiolanes |
| Target Id | NPT204, NPT31, NPT483, NPT50, NPT46, NPT796, NPT58, NPT543, NPT160 |
| Xlogp | 1.7 |
| Superclass | Organoheterocyclic compounds |
| Subclass | Lipoic acids and derivatives |
| Molecular Formula | C8H14O2S2 |
| Prediction Swissadme | 1.0 |
| Inchi Key | AGBQKNBQESQNJD-SSDOTTSWSA-N |
| Fcsp3 | 0.875 |
| Logs | -2.857 |
| Rotatable Bond Count | 5.0 |
| State | Solid |
| Logd | 1.385 |
| Synonyms | (+-)-1,2-Dithiolane-3-pentanoate, (+-)-1,2-Dithiolane-3-pentanoic acid, (+-)-1,2-Dithiolane-3-valerate, (+-)-1,2-Dithiolane-3-valeric acid, (+)-alpha-Lipoate, (+)-alpha-Lipoic acid, (R)-1,2-Dithiolane-3-pentanoate, (R)-1,2-Dithiolane-3-pentanoic acid, (RS)-alpha-Lipoate, (RS)-alpha-Lipoic acid, (RS)-Lipoate, (RS)-Lipoic acid, (S)-(−)-lipoic acid, (S)-1,2-Dithiolane-3-pentanoic acid, (S)-alpha-Lipoic acid, 1,2-Dithiolane-3-pentanoate, 1,2-Dithiolane-3-pentanoic acid, 1,2-Dithiolane-3-valerate, 1,2-Dithiolane-3-valeric acid, 1,2-Dithiolane-3R-pentanoate, 1,2-Dithiolane-3R-pentanoic acid, 5-(1,2-Dithiolan-3-yl)pentanoate, 5-(1,2-Dithiolan-3-yl)pentanoic acid, 5-(1,2-Dithiolan-3-yl)valerate, 5-(1,2-Dithiolan-3-yl)valeric acid, 5-(Dithiolan-3-yl)valerate, 5-(Dithiolan-3-yl)valeric acid, 5-[3-(1,2-dithiolanyl)]pentanoate, 5-[3-(1,2-dithiolanyl)]pentanoic acid, 6-Thioctate, 6-Thioctic acid, 6-Thiotate, 6-Thiotic acid, 6,8-Dithiooctanoate, 6,8-Dithiooctanoic acid, 6,8-Thioctate, 6,8-Thioctic acid, 6,8-Thiotate, 6,8-Thiotic acid, acetate replacing factor, Acetate-replacing factor, alpha Lipoate, alpha Lipoic acid, alpha-Liponate, alpha-Liponic acid, alpha-Liponsaeure, Biletan, delta-[3-(1,2-dithiacyclopentyl)]pentanoate, delta-[3-(1,2-dithiacyclopentyl)]pentanoic acid, DL-1,2-Dithiolane 3-valerate, DL-1,2-Dithiolane 3-valeric acid, DL-6-Thioctate, DL-6-Thioctic acid, DL-6,8-Dithiooctanoate, DL-6,8-Dithiooctanoic acid, DL-6,8-Thioctate, DL-6,8-Thioctic acid, DL-alpha-Lipoate, DL-alpha-Lipoic acid, dl-Lipoate, dl-Lipoic acid, dl-Thioctate, dl-Thioctic acid, DL-Thioctic acid > 98%, Heparlipon, L-1,2-Dithiolane 3-valeric acid, L-6-Thioctic acid, L-6,8-Thioctic acid, Lip, Lipoate, Lipoic acid, liponate, liponic acid, Liposan, Lipothion, Protogen A, Pyruvate oxidation factor, R-Lipoate, R-Lipoic acid, Rac-lipoate, Rac-lipoic acid, S-LA, SLA, Thioctacid, Thioctan, Thioctate, Thioctic acid, Thioctic acid d-form, Thioctic acid dl-form, Thioctic acid L-form, Thioctidase, Thioctsan, Thioktsaeure, Thiooctanoate, Thiooctanoic acid, Tioctacid, Tioctan, Tioctidasi, Tioctidasi acetate replacing factor, (R)-(+)-Lipoate, (R)-(+)-Lipoic acid, (R)-1,2-Dithiolane-3-valeric acid, (R)-6,8-Thioctic acid, alpha-Lipoic acid, R-(+)-Lipoic acid, R-LA, RLA, Thioctic acid D-form, (+)-a-Lipoate, (+)-a-Lipoic acid, (+)-α-lipoate, (+)-α-lipoic acid, (R)-Lipoate, (R)-1,2-Dithiolane-3-valerate, (R)-6,8-Thioctate, a-Lipoate, a-Lipoic acid, alpha-Lipoate, α-lipoate, α-Lipoic acid, R-(+)-Lipoate, Thioctate D-form, Acid, alpha-lipoic, (R)-Lipoic acid, (3R)-1,2-Dithiolane-3-pentanoic acid, (R)-(+)-1,2-Dithiolane-3-pentanoic acid, (R)-(+)-alpha-Lipoic acid, (R)-(+)-α-Lipoic acid, (R)-5-(1,2-Dithiolan-3-yl)pentanoicacid, (R)-alpha-Lipoic acid, (R)-α-Lipoic acid, ALA, alpha-(+)-Lipoic acid, α-(+)-Lipoic acid |
| Substituent Name | Lipoic_acid_derivative, Medium-chain fatty acid, Thia fatty acid, Heterocyclic fatty acid, Fatty acyl, Fatty acid, 1,2-dithiolane, Organic disulfide, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aliphatic heteromonocyclic compound |
| Compound Name | Lipoic acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 1.0 |
| Exact Mass | 206.044 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 206.044 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 206.3 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Esol | -1.8476583999999998 |
| Inchi | 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 |
| Smiles | C1CSS[C@@H]1CCCCC(=O)O |
| Nring | 1.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Lipoic acids and derivatives |
- 1. Outgoing r'ship
FOUND_INto/from Liriodendron Tulipifera (Plant) Rel Props:Source_db:cmaup_ingredients