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lipoate (M2MDB003418)

Record Information
Version2.0
Creation Date2012-10-10 12:13:10 -0600
Update Date2015-08-05 16:22:03 -0600
Secondary Accession Numbers
  • ECMDB23028
Identification
Name:lipoate
DescriptionA thia fatty acid anion that is the conjugate base of lipoic acid; major species at pH 7.3.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI 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
  • 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
  • 6,8-Thioctate
  • 6,8-Thioctic acid
  • 6,8-Thiotate
  • 6,8-Thiotic acid
  • 6-Thioctate
  • 6-Thioctic acid
  • 6-Thiotate
  • 6-Thiotic acid
  • a-Lipoate
  • a-Lipoic acid
  • a-Liponsaeure
  • Acetate-replacing factor
  • Acetic acid-replacing factor
  • alpha-Lipoate
  • alpha-Lipoic acid
  • alpha-Liponsaeure
  • Biletan
  • Lipoic acid
  • Liponate
  • Liponic acid
  • Thioctansaeure
  • Thioctate
  • Thioctic acid
  • Thioctsaeure
  • Thioktsaeure
  • α-Lipoate
  • α-Lipoic acid
  • α-Liponsaeure
Chemical Formula:C8H14O2S2
Weight:Average: 206.326
Monoisotopic: 206.043521072
InChI Key:AGBQKNBQESQNJD-UHFFFAOYSA-N
InChI:InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
CAS number:62-46-4
IUPAC Name:5-(1,2-dithiolan-3-yl)pentanoic acid
Traditional IUPAC Name:6,8-thioctic acid
SMILES:OC(=O)CCCCC1CCSS1
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoic acids and derivatives
Direct ParentLipoic 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:2.24e-01 g/lPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.75ALOGPS
logP2.11ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.37 m³·mol⁻¹ChemAxon
Polarizability22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + lipoate > Pyrophosphate + Lipoyl-AMP
Adenosine triphosphate + lipoate + Lipoyl-AMP + Apoprotein <> Pyrophosphate + Protein N6-(lipoyl)lysine + Adenosine monophosphate
lipoate + Adenosine triphosphate > Lipoyl-AMP + Pyrophosphate + Lipoyl-AMP
SMPDB Pathways:
Lipoic acid metabolismPW000770 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4900000000-59fc063b5aa5a8b5db19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-50da42c94591e9a60c0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-1346e3a528dca0514cf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03di-9000000000-420a38a26d85b4091edbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-9000000000-24b63eebe2fd067ce4b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0229-6900000000-44bcc93e18aeabd9ee16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03k9-9600000000-4f680dfeae7fa1ece57aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-03di-9000000000-6f0b91016a33e202e49bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03di-9000000000-e3d4a7fe022cf20db036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920000000-cf913d1d1afc04e5450cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-5910000000-294c510229247ef63f20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9600000000-f8f54eb79c5d4d5bef48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0920000000-5a823a30dd1fb434e5b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmu-1910000000-6f491a68afd82922e71bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-330e4766f82ed571497bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0970000000-0ae5b11a032d11c1ba6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-decf255617c1bbd69bfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-eb58a3d8135ba85d4283View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-014d2ea36cfae0726a9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9500000000-9bbbd7b252fb9a0b438dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16494
HMDB IDHMDB14312
Pubchem Compound ID864
Kegg IDC00725
ChemSpider ID841
WikipediaLipoic_Acid
BioCyc IDNot Available

Enzymes

Protein Details
1. 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. Is also able to catalyze very poorly the transfer of lipoyl and octanoyl moiety from their acyl carrier protein
Gene Name:
lplA
Uniprot ID:
P32099
Molecular weight:
37926
Reactions
ATP + lipoate = diphosphate + lipoyl-AMP.
Lipoyl-AMP + protein = protein N(6)-(lipoyl)lysine + AMP.