Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110217
Identification
Name: lipoamide
Description:A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia.
Structure
Thumb
Synonyms:
  • 5-(1,2-dithiolan-3-yl)-pentanamide
  • DL-lipoamide
  • 6,8-dithiooctanoic amide
Chemical Formula: C8H15NOS2
Average Molecular Weight: 205.33
Monoisotopic Molecular Weight: 205.0595054888
InChI Key: FCCDDURTIIUXBY-SSDOTTSWSA-N
InChI: InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)/t7-/m1/s1
CAS number: 940-69-2
IUPAC Name:5-(1,2-dithiolan-3-yl)pentanamide
Traditional IUPAC Name: lipoamide
SMILES:C1(CC(CCCCC(N)=O)SS1)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as lipoamides. These are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassDithiolanes
Direct Parent Lipoamides
Alternative Parents
Substituents
  • Lipoamide
  • Fatty amide
  • Fatty acyl
  • 1,2-dithiolane
  • Carboxamide group
  • Organic disulfide
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 126.0 - 129.0 °C
Experimental Properties:
PropertyValueReference
Melting Point126.0 - 129.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 mg/mLALOGPS
logP2.3ALOGPS
logP1.31ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.19 m3·mol-1ChemAxon
Polarizability22.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-6963000000-7e1887d53c2801b09961View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017l-3920000000-a3a7a08acf06d41c9b73View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-24fca44fc025dbd6be18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ziu-9700000000-7dfd23f450bdfd581100View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056u-9000000000-13583c4eb6b06a56c392View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-052r-2920000000-a4fb7176abf63e581f5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-2900000000-10a079a84f024494ae23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0zfr-9800000000-b01332176d6829b1eaa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udl-9400000000-7a03c741edae36dff9cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a5c-9100000000-7b44dfbfcbb0cc516254View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-50512172ce038bce2995View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-7652a33c17a37b6914aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-0df59a6540bede8a4a79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Przybyla-Zawislak B, Gadde DM, Ducharme K, McCammon MT (1999)Genetic and biochemical interactions involving tricarboxylic acid cycle (TCA) function using a collection of mutants defective in all TCA cycle genes. Genetics 152, Pubmed: 10224250
  • Shen W, Hao J, Feng Z, Tian C, Chen W, Packer L, Shi X, Zang W, Liu J (2011)Lipoamide or lipoic acid stimulates mitochondrial biogenesis in 3T3-L1 adipocytes via the endothelial NO synthase-cGMP-protein kinase G signalling pathway. British journal of pharmacology 162, Pubmed: 21108628
  • Feeney MA, Veeravalli K, Boyd D, Gon S, Faulkner MJ, Georgiou G, Beckwith J (2011)Repurposing lipoic acid changes electron flow in two important metabolic pathways of Escherichia coli. Proceedings of the National Academy of Sciences of the United States of America 108, Pubmed: 21521794
Synthesis Reference: Xu, Yaming; Li, Zhitian; Gu, Yunlong. Synthesis of thioctamide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1997), 5 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS940-69-2
ChEBI6491
ChemSpider5360246
HMDBHMDB00962
KEGGC00248
PubChem6992093