ChemFOnt: Showing chemical card for alpha-Lipoic acid (CFc000333488)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:37 UTC

Chemfont ID

CFc000333488

Molecule Identification

Common Name

alpha-Lipoic acid

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dithiolane-3-pentanoic acid	ChEBI
1,2-Dithiolane-3-valeric acid	ChEBI
5-(1,2-Dithiolan-3-yl)valeric acid	ChEBI
5-(Dithiolan-3-yl)valeric acid	ChEBI
5-[3-(1,2-Dithiolanyl)]pentanoic acid	ChEBI
6,8-Thioctic acid	ChEBI
6,8-Thiotic acid	ChEBI
6-Thioctic acid	ChEBI
6-Thiotic acid	ChEBI
Acetate-replacing factor	ChEBI
alpha-Lipoic acid	ChEBI
alpha-Liponsaeure	ChEBI
Biletan	ChEBI
Liponic acid	ChEBI
Thioctansaeure	ChEBI
Thioctic acid	ChEBI
Thioctsaeure	ChEBI
Thioktsaeure	ChEBI
Thiotomin	Kegg
Lipoic acid	Kegg
DL-alpha-Lipoic acid	Kegg
DL-Thioctic acid	Kegg
1,2-Dithiolane-3-pentanoate	Generator
1,2-Dithiolane-3-valerate	Generator
5-(1,2-Dithiolan-3-yl)valerate	Generator
5-(Dithiolan-3-yl)valerate	Generator
5-[3-(1,2-Dithiolanyl)]pentanoate	Generator
6,8-Thioctate	Generator
6,8-Thiotate	Generator
6-Thioctate	Generator
6-Thiotate	Generator
Acetic acid-replacing factor	Generator
a-Lipoate	Generator
a-Lipoic acid	Generator
alpha-Lipoate	Generator
Α-lipoate	Generator
Α-lipoic acid	Generator
a-Liponsaeure	Generator
Α-liponsaeure	Generator
Liponate	Generator
Thioctate	Generator
DL-a-Lipoate	Generator
DL-a-Lipoic acid	Generator
DL-alpha-Lipoate	Generator
DL-Α-lipoate	Generator
DL-Α-lipoic acid	Generator
DL-Thioctate	Generator
Acid, alpha-lipoic	MeSH
Alpha Lipogamma	MeSH
Alpha Lipon stada	MeSH
Alpha Liponsaure sofotec	MeSH
Alpha Lippon al	MeSH
Alpha-Lipogamma	MeSH
Alpha-Lipon stada	MeSH
Alpha-Liponsaure sofotec	MeSH
Alpha-Lippon al	MeSH
AlphaLipogamma	MeSH
AlphaLipon stada	MeSH
AlphaLiponsaure sofotec	MeSH
AlphaLippon al	MeSH
Alphaflam	MeSH
Azulipont	MeSH
Fenint	MeSH
Injekt, thiogamma	MeSH
Juthiac	MeSH
Liponsaure ratiopharm	MeSH
Liponsaure-ratiopharm	MeSH
Liponsaureratiopharm	MeSH
MTW Alphaliponsaure	MeSH
MTW-Alphaliponsaure	MeSH
MTWAlphaliponsaure	MeSH
Neurium	MeSH
Pleomix Alpha	MeSH
Pleomix Alpha N	MeSH
Pleomix-Alpha	MeSH
Pleomix-Alpha N	MeSH
PleomixAlpha	MeSH
PleomixAlpha N	MeSH
Thioctacid	MeSH
Thioctacide T	MeSH
Thiogamma injekt	MeSH
Thiogamma oral	MeSH
Tromlipon	MeSH
Verla lipon	MeSH
Verla-lipon	MeSH
VerlaLipon	MeSH
alpha Lipoic acid	MeSH
alpha Liponaure heumann	MeSH
alpha Liponsaure von CT	MeSH
alpha Vibolex	MeSH
alpha-Liponaure heumann	MeSH
alpha-Liponsaure von CT	MeSH
alpha-Vibolex	MeSH
AlphaLiponaure heumann	MeSH
AlphaLiponsaure von CT	MeSH
AlphaVibolex	MeSH
Biomo lipon	MeSH
Biomo-lipon	MeSH
Biomolipon	MeSH
Duralipon	MeSH
Espa lipon	MeSH
Espa-lipon	MeSH
Espalipon	MeSH
(R)-Lipoate	Generator
Generosan brand OF thioctic acid	MeSH
Merck dura brand OF thioctic acid	MeSH
Rosen brand OF thioctic acid	MeSH
Trommsdorgg brand OF thioctic acid	MeSH
Viatris brand OF thioctic acid tromethamine	MeSH
Esparma brand OF thioctic acid	MeSH
Hexal brand OF thioctic acid	MeSH
Stadapharm brand OF thioctic acid	MeSH
Viatris brand OF thioctic acid	MeSH
Ratiopharm brand OF thioctic acid	MeSH
Aliud brand OF thioctic acid	MeSH
Illa brand OF thioctic acid	MeSH
Illa brand OF thioctic acid tromethamine	MeSH
MTW Brand OF thioctic acid	MeSH
Pharmacia brand OF thioctic acid	MeSH
Q Pharm brand OF thioctic acid	MeSH
Q-Pharm brand OF thioctic acid	MeSH
Azupharma brand OF thioctic acid	MeSH
Heumann brand OF thioctic acid	MeSH
Juta brand OF thioctic acid	MeSH
Lichtenstein brand OF thioctic acid	MeSH
Sofotec brand OF thioctic acid	MeSH
Verla brand OF thioctic acid	MeSH
Worwag brand OF thioctic acid	MeSH
Worwag brand OF thioctic acid meglumine	MeSH
biomo Brand OF thioctic acid	MeSH
CT Arzneimittel brand OF thioctic acid	MeSH
CT-Arzneimittel brand OF thioctic acid	MeSH

Chemical Formula

C₈H₁₄O₂S₂

Average Molecular Weight

206.326

Monoisotopic Molecular Weight

206.043521072

IUPAC Name

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

Traditional Name

6,8-thioctic acid

CAS Registry Number

62-46-4

SMILES

OC(=O)CCCCC1CCSS1

InChI Identifier

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

InChI Key

AGBQKNBQESQNJD-UHFFFAOYSA-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:16494 )
thia fatty acid (CHEBI:16494 )
heterocyclic fatty acid (CHEBI:16494 )
Prosthetic group [Fig] (C00725 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0001451)

Food

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Spinach (FooDB: FOOD00178)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0001451)
Antioxidant (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	22 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