Lipoic acid (YMDB00334)

Identification

YMDB ID

YMDB00334

Name

Lipoic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

(R)-lipoic acid, also known as RLA or a-lipoate, 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 (R)-lipoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-lipoic acid exists in all living species, ranging from bacteria to humans.

Structure

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

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
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-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
Lip
Lipoate
Lipoic acid
liponate
liponic acid
Liposan
Lipothion
Protogen A
Pyruvate oxidation factor
R-Lipoate
R-Lipoic acid
Rac-lipoate
Rac-lipoic acid
Thioctacid
Thioctan
Thioctate
Thioctic acid
Thioctic acid d-form
Thioctic acid dl-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
R-(+)-Lipoic acid
R-LA
RLA
(+)-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
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

CAS number

1077-28-7

Weight

Average: 206.326
Monoisotopic: 206.043521072

InChI Key

AGBQKNBQESQNJD-SSDOTTSWSA-N

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

IUPAC Name

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

Traditional IUPAC Name

lipoic acid

Chemical Formula

C₈H₁₄O₂S₂

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])SSC([H])([H])C1([H])[H]

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 )

Physical Properties

State

Solid

Charge

Melting point

60.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Lipoic acid metabolism

PW002499

KEGG Pathways

Lipoic acid metabolism

ec00785

SMPDB Reactions

Lipoic acid + Adenosine triphosphate → Pyrophosphate + lipoyl-AMP

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aba-3900000000-46fc1d57abcc26f6720e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aba-3900000000-46fc1d57abcc26f6720e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aba-3900000000-46fc1d57abcc26f6720e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aba-3900000000-46fc1d57abcc26f6720e	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufu-5900000000-716655e029db4b97efd9	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0hbi-6920000000-011fb15a0f9ca4513029	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4r-0940000000-dead1b29e79e0002da2a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0f8c-9200000000-b6035bdb4abd0d267297	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0059-9000000000-62e73cabbac1531f5145	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9100000000-e420d2c931e889befcfa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0229-6900000000-90386d8704ab5bfe8e70	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-042d27906c9bde31821f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-9000000000-6572cec5a1c9f68d9679	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0940000000-6cecd351951f396a3035	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08gr-6910000000-f169816d57d2290b0d9e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0m2c-9700000000-57ae386a681b98208a4b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1920000000-2b265e3ed116fbc0a2ea	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-2910000000-9142e84d978f4a481551	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-8bdfe1c35977a8c80985	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0970000000-0ae5b11a032d11c1ba6d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-decf255617c1bbd69bfb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-6900000000-eb58a3d8135ba85d4283	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-014d2ea36cfae0726a9e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9500000000-9bbbd7b252fb9a0b438d	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	30314
HMDB ID	HMDB01451
Pubchem Compound ID	864
Kegg ID	C00725
ChemSpider ID	5886
FOODB ID	FDB022631
Wikipedia	Lipoic_acid
BioCyc ID	LIPOIC-ACID

Enzymes

Protein Details

1. Putative lipoate-protein ligase A

General function:: Involved in catalytic activity
Specific function:: Catalyzes both the ATP-dependent activation of exogenously supplied lipoate to lipoyl-AMP and the transfer of the activated lipoyl onto the lipoyl domains of lipoate-dependent enzymes
Gene Name:: AIM22
Uniprot ID:: P47051
Molecular weight:: 47003.0

Reactions

ATP + lipoate → diphosphate + lipoyl-AMP.
Lipoyl-AMP + protein → protein N(6)-(lipoyl)lysine + AMP.

Structure for #<Compound:0xa3618070>

Enzymes

Reactions