ContaminantDB: alpha-Lipoic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:56:25 UTC

Update Date

2016-11-09 01:15:31 UTC

Accession Number

CHEM017109

Identification

Common Name

alpha-Lipoic acid

Class

Small Molecule

Description

A heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position.

Contaminant Sources

FooDB Chemicals
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Mass

206.326 g/mol

Monoisotopic Mass

206.044 g/mol

CAS Registry Number

1077-28-7

IUPAC Name

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

Traditional Name

6,8-thioctic acid

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4900000000-59fc063b5aa5a8b5db19	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-50da42c94591e9a60c0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-1346e3a528dca0514cf7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-03di-9000000000-420a38a26d85b4091edb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03di-9000000000-24b63eebe2fd067ce4b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0229-6900000000-44bcc93e18aeabd9ee16	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03k9-9600000000-4f680dfeae7fa1ece57a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03di-9000000000-6f0b91016a33e202e49b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03di-9000000000-e3d4a7fe022cf20db036	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0920000000-cf913d1d1afc04e5450c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bti-5910000000-294c510229247ef63f20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9600000000-f8f54eb79c5d4d5bef48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0920000000-5a823a30dd1fb434e5b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kmu-1910000000-6f491a68afd82922e71b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-330e4766f82ed571497b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0970000000-0ae5b11a032d11c1ba6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-decf255617c1bbd69bfb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-6900000000-eb58a3d8135ba85d4283	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-014d2ea36cfae0726a9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9500000000-9bbbd7b252fb9a0b438d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum