NP-MRD: Showing NP-Card for Lipoic acid (NP0137497)

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Record Information

Version

2.0

Created at

2022-05-30 16:54:12 UTC

Updated at

2022-05-30 16:54:12 UTC

NP-MRD ID

NP0137497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lipoic acid

Description

Lipoate, also known as lipoic acid or 6,8-thioctic acid, 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. Lipoate is a weakly acidic compound (based on its pKa). Lipoate may be a unique E. Coli metabolite. In humans, lipoate is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Outside of the human body, lipoate has been detected, but not quantified in, broccoli and spinachs. This could make lipoate a potential biomarker for the consumption of these foods. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. Lipoic acid is found in Hyacinthoides non-scripta. Lipoic acid was first documented in 1994 (PMID: 7519986). Lipoate is a potentially toxic compound (PMID: 7548757).

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -0.057   1.312   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       0.713  -1.058   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.303   0.406   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      -0.827  -1.058   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       1.188   0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.522   1.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.856   0.406   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.190   1.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.523   0.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.857   1.176   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.857   2.716   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.191   0.406   0.000  0.00  0.00           O+0
CONECT    1    5    3                                                       
CONECT    2    5    4                                                       
CONECT    3    1    4                                                       
CONECT    4    2    3                                                       
CONECT    5    1    2    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

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
Lipoic acid	Kegg
DL-alpha-Lipoic acid	Kegg
DL-Thioctic acid	Kegg
Thiotomin	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
(R)-Lipoate	Generator
Alpha Lipogamma	MeSH
Alpha Liponsaure sofotec	MeSH
Alpha-Lipogamma	MeSH
Alpha-Lippon al	MeSH
AlphaLipogamma	MeSH
Alphaflam	MeSH
Generosan brand OF thioctic acid	MeSH
Juthiac	MeSH
Liponsaure-ratiopharm	MeSH
Liponsaureratiopharm	MeSH
Merck dura brand OF thioctic acid	MeSH
Pleomix Alpha N	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
alpha Lipoic acid	MeSH
alpha-Liponsaure von CT	MeSH
AlphaLiponaure heumann	MeSH
AlphaLiponsaure von CT	MeSH
biomo Lipon	MeSH
Esparma brand OF thioctic acid	MeSH
Acid, alpha-lipoic	MeSH
Alpha Lipon stada	MeSH
Alpha Lippon al	MeSH
AlphaLipon stada	MeSH
AlphaLiponsaure sofotec	MeSH
AlphaLippon al	MeSH
Hexal brand OF thioctic acid	MeSH
Injekt, thiogamma	MeSH
Liponsaure ratiopharm	MeSH
Pleomix Alpha	MeSH
Stadapharm brand OF thioctic acid	MeSH
Thioctacide T	MeSH
Viatris brand OF thioctic acid	MeSH
alpha Liponsaure von CT	MeSH
AlphaVibolex	MeSH
Biomolipon	MeSH
Ratiopharm brand OF thioctic acid	MeSH
Aliud brand OF thioctic acid	MeSH
Alpha-Liponsaure sofotec	MeSH
Azulipont	MeSH
Illa brand OF thioctic acid	MeSH
Illa brand OF thioctic acid tromethamine	MeSH
MTW Alphaliponsaure	MeSH
MTW Brand OF thioctic acid	MeSH
Pharmacia brand OF thioctic acid	MeSH
Pleomix-Alpha	MeSH
PleomixAlpha	MeSH
PleomixAlpha N	MeSH
Q Pharm brand OF thioctic acid	MeSH
Q-Pharm brand OF thioctic acid	MeSH
Verla lipon	MeSH
Verla-lipon	MeSH
alpha Liponaure heumann	MeSH
alpha Vibolex	MeSH
biomo-Lipon	MeSH
Duralipon	MeSH
Alpha-Lipon stada	MeSH
Azupharma brand OF thioctic acid	MeSH
Fenint	MeSH
Heumann brand OF thioctic acid	MeSH
Juta brand OF thioctic acid	MeSH
Lichtenstein brand OF thioctic acid	MeSH
MTW-Alphaliponsaure	MeSH
MTWAlphaliponsaure	MeSH
Neurium	MeSH
Sofotec brand OF thioctic acid	MeSH
Thioctacid	MeSH
Thiogamma injekt	MeSH
Verla brand OF thioctic acid	MeSH
VerlaLipon	MeSH
Worwag brand OF thioctic acid	MeSH
Worwag brand OF thioctic acid meglumine	MeSH
alpha-Liponaure heumann	MeSH
alpha-Vibolex	MeSH
biomo Brand OF thioctic acid	MeSH
CT Arzneimittel brand OF thioctic acid	MeSH
CT-Arzneimittel brand OF thioctic acid	MeSH
Espa lipon	MeSH
Espa-lipon	MeSH
Espalipon	MeSH

Chemical Formula

C₈H₁₄O₂S₂

Average Mass

206.3260 Da

Monoisotopic Mass

206.04352 Da

IUPAC Name

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

Traditional Name

6,8-thioctic acid

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hyacinthoides non-scripta	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB004339

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00725

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lipoic_acid

METLIN ID

Not Available

PubChem Compound

864

PDB ID

Not Available

ChEBI ID

16494

Good Scents ID

Not Available

References

General References

Christen U, Quinn J, Yeaman SJ, Kenna JG, Clarke JB, Gandolfi AJ, Gut J: Identification of the dihydrolipoamide acetyltransferase subunit of the human pyruvate dehydrogenase complex as an autoantigen in halothane hepatitis. Molecular mimicry of trifluoroacetyl-lysine by lipoic acid. Eur J Biochem. 1994 Aug 1;223(3):1035-47. doi: 10.1111/j.1432-1033.1994.tb19082.x. [PubMed:7519986 ]
Frey N, Christen U, Jeno P, Yeaman SJ, Shimomura Y, Kenna JG, Gandolfi AJ, Ranek L, Gut J: The lipoic acid containing components of the 2-oxoacid dehydrogenase complexes mimic trifluoroacetylated proteins and are autoantigens associated with halothane hepatitis. Chem Res Toxicol. 1995 Jul-Aug;8(5):736-46. doi: 10.1021/tx00047a014. [PubMed:7548757 ]

Showing NP-Card for Lipoic acid (NP0137497)

MOL for NP0137497 (Lipoic acid)

3D MOL for NP0137497 (Lipoic acid)

3D SDF for NP0137497 (Lipoic acid)

3D-SDF for NP0137497 (Lipoic acid)

PDB for NP0137497 (Lipoic acid)

3D PDB for NP0137497 (Lipoic acid)

SMILES for NP0137497 (Lipoic acid)

INCHI for NP0137497 (Lipoic acid)

Structure for NP0137497 (Lipoic acid)

3D Structure for NP0137497 (Lipoic acid)