Showing metabocard for Lipoamide (BMDB0000962)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
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Record Information
Version1.0
Creation Date2016-09-30 22:39:13 UTC
Update Date2020-05-21 16:28:44 UTC
BMDB IDBMDB0000962
Secondary Accession Numbers
  • BMDB00962
Metabolite Identification
Common NameLipoamide
DescriptionLipoamidee, also known as lipoamidee or lipoamidee, belongs to the class of organic compounds known as lipoamidees. Lipoamidees are compounds containing a lipoamidee moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring. Thus, lipoamidee is considered to be a fatty amide lipid molecule. Lipoamidee exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lipoamidee exists in all living species, ranging from bacteria to humans. In cattle, lipoamidee is involved in the metabolic pathway called the citric Acid cycle pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC8H15NOS2
Average Molecular Weight205.341
Monoisotopic Molecular Weight205.059505487
IUPAC Name5-(1,2-dithiolan-3-yl)pentanamide
Traditional Namelipoamide
CAS Registry Number940-69-2
SMILES
NC(=O)CCCCC1CCSS1
InChI Identifier
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
InChI KeyFCCDDURTIIUXBY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoamides
Direct ParentLipoamides
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point126.0 - 129.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.3ALOGPS
logP1.31ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.19 m³·mol⁻¹ChemAxon
Polarizability22.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-6963000000-7e1887d53c2801b09961View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017l-3920000000-a3a7a08acf06d41c9b73View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1910000000-b6ee336856e354af8114View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-3900000000-60cad9dd198c3ad64ed7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-9800000000-ac967ad86beefc26c983View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052r-2920000000-a4fb7176abf63e581f5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-158c946037c5d7bb3e50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-9800000000-b01332176d6829b1eaa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udl-9400000000-7a03c741edae36dff9cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5c-9100000000-7b44dfbfcbb0cc516254View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-fa779b1c88469a732321View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1900000000-9e4b6873b24c66cf9f69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0900000000-b37ce6b25b9feef09b96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0940000000-d79e1aa52057e567d71fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3900000000-abd8148048c5f282d889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adr-9500000000-9769c619660ab6af46d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zml-1920000000-79d57d488cb8fbc804a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdo-4910000000-d264eaf6e242c36bc563View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-289d2f20046f7819a7caView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, methanol, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, methanol, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000962
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022340
KNApSAcK IDNot Available
Chemspider ID840
KEGG Compound IDC00248
BioCyc IDLIPOAMIDE
BiGG ID34384
Wikipedia LinkLipoamide
METLIN ID3372
PubChem Compound863
PDB IDNot Available
ChEBI ID17460
References
Synthesis ReferenceXu, Yaming; Li, Zhitian; Gu, Yunlong. Synthesis of thioctamide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1997), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Energy production and conversion
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P11178
Molecular weight:
51678.0
Reactions
3-Methyl-1-hydroxybutyl-ThPP + Lipoamide → S-(3-Methylbutanoyl)-dihydrolipoamide-Edetails
Lipoamide → S-(2-Methylpropionyl)-dihydrolipoamide-Edetails
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Energy production and conversion
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21839
Molecular weight:
42935.0
Reactions
3-Methyl-1-hydroxybutyl-ThPP + Lipoamide → S-(3-Methylbutanoyl)-dihydrolipoamide-Edetails
Lipoamide → S-(2-Methylpropionyl)-dihydrolipoamide-Edetails
Enzyme Details
3. Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
General function:
Energy production and conversion
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA1
Uniprot ID:
A7MB35
Molecular weight:
43388.0
Reactions
Pyruvic acid + Lipoamide → S-Acetyldihydrolipoamide-E + Carbon dioxidedetails
Enzyme Details
4. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
General function:
Energy production and conversion
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHB
Uniprot ID:
P11966
Molecular weight:
39126.0
Reactions
Pyruvic acid + Lipoamide → S-Acetyldihydrolipoamide-E + Carbon dioxidedetails