ChemFOnt: Showing chemical card for (R)-Lipoic acid (CFc000001120)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:41 UTC

Chemfont ID

CFc000001120

Molecule Identification

Common Name

(R)-Lipoic acid

Definition

Lipoic acid is 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-alpha-Lipoic acid	ChEBI, HMDB
(R)-(+)-Lipoate	ChEBI, KEGG
(R)-(+)-Lipoic acid	ChEBI, Generator
(R)-1,2-Dithiolane-3-pentanoic acid	ChEBI, HMDB
(R)-1,2-Dithiolane-3-valeric acid	ChEBI, HMDB
(R)-6,8-Thioctic acid	ChEBI, HMDB
alpha-Lipoic acid	ChEBI, HMDB
Lipoic acid	ChEBI, HMDB
R-(+)-Lipoic acid	ChEBI, KEGG
R-LA	ChEBI, HMDB
RLA	ChEBI, HMDB
Thioctic acid	ChEBI, HMDB
Thioctic acid D-form	ChEBI, HMDB
(+)-a-Lipoate	Generator, HMDB
(+)-a-Lipoic acid	Generator, HMDB
(+)-alpha-Lipoate	Generator, HMDB
(+)-α-lipoate	Generator, HMDB
(+)-α-lipoic acid	Generator, HMDB
(R)-Lipoate	Generator
(R)-1,2-Dithiolane-3-pentanoate	Generator, HMDB
(R)-1,2-Dithiolane-3-valerate	Generator, HMDB
(R)-6,8-Thioctate	Generator, HMDB
a-Lipoate	Generator, HMDB
a-Lipoic acid	Generator, HMDB
alpha-Lipoate	Generator, HMDB
α-lipoate	Generator, HMDB
α-Lipoic acid	Generator, HMDB
Lipoate	Generator, HMDB
R-(+)-Lipoate	Generator
Thioctate	Generator, HMDB
Thioctate D-form	Generator, HMDB
Acid, alpha-lipoic	MeSH, HMDB
alpha Lipoic acid	MeSH, HMDB
1,2-Dithiolane-3R-pentanoic acid	KEGG
1,2-Dithiolane-3R-pentanoate	Generator
(R)-Lipoic acid	KEGG
(3R)-1,2-Dithiolane-3-pentanoic acid	HMDB
(R)-(+)-1,2-Dithiolane-3-pentanoic acid	HMDB
(R)-(+)-alpha-Lipoic acid	HMDB
(R)-(+)-α-Lipoic acid	HMDB
(R)-5-(1,2-Dithiolan-3-yl)pentanoicacid	HMDB
(R)-alpha-Lipoic acid	HMDB
(R)-α-Lipoic acid	HMDB
ALA	HMDB
alpha-(+)-Lipoic acid	HMDB
α-(+)-Lipoic acid	HMDB
1,2-Dithiolane-3-valeric 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

Chemical Formula

C₈H₁₄O₂S₂

Average Molecular Weight

206.326

Monoisotopic Molecular Weight

206.043521072

IUPAC Name

5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid

Traditional Name

lipoic acid

CAS Registry Number

1200-22-2

SMILES

OC(=O)CCCC[C@@H]1CCSS1

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

InChI Key

AGBQKNBQESQNJD-SSDOTTSWSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoic acids and derivatives

Direct Parent

Lipoic acids and derivatives

Alternative Parents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dithiolanes (CHEBI:30314 )
thia fatty acid (CHEBI:30314 )
heterocyclic fatty acid (CHEBI:30314 )
lipoic acid (CHEBI:30314 )
Thia fatty acids (C16241 )
Thia fatty acids (LMFA01130001 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Tissue substructure

Muscle (HMDB: HMDB0001451)

Skeletal muscle (HMDB: HMDB0001451)
Skeletal muscle (HMDB: HMDB0001451)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0001451)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0001451)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Ammonia Recycling (HMDB: HMDB0001451)
Glycine and Serine Metabolism (HMDB: HMDB0001451)
Ammonia Recycling (HMDB: HMDB0001451)
Lipoic Acid Metabolism (PathBank: SMP0000793)
Arsenate Detoxification (PathBank: SMP0121123)
Citrate Cycle (PathBank: SMP0121182)

Disease pathway

Sarcosinemia (PathBank: SMP0120521)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD) (PathBank: SMP0120694)
Non-Ketotic Hyperglycinemia (PathBank: SMP0120534)
3-Phosphoglycerate Dehydrogenase Deficiency (PathBank: SMP0120872)
Hyperglycinemia, Non-Ketotic (PathBank: SMP0120770)
Dimethylglycine Dehydrogenase Deficiency (PathBank: SMP0120695)

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0001451)

Food and nutrition

Nutritional supplement (HMDB: HMDB0001451)

Nutraceutical (HMDB: HMDB0001451)

Biological role

Prosthetic group (HMDB: HMDB0001451)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.11	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	54.37 m³·mol⁻¹	ChemAxon
Polarizability	21.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon