lipoyl-AMP (YMDB00239)

Identification
YMDB IDYMDB00239
Namelipoyl-AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionLipoyl-AMP belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. Lipoyl-AMP is a strong basic compound (based on its pKa). lipoyl-AMP can be biosynthesized from lipoate; which is catalyzed by the enzyme lipoate-protein ligase a. In yeast, lipoyl-AMP is involved in the metabolic pathway called the lipoic acid metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Lipoyl-AMP
CAS numberNot Available
WeightAverage: 535.532
Monoisotopic: 535.096040725
InChI KeyQWEGOCJRZOKSOE-NLJBGGCZSA-N
InChIInChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid
Traditional IUPAC NameLipoyl-AMP
Chemical FormulaC18H26N5O8PS2
SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent5'-acylphosphoadenosines
Alternative Parents
Substituents
  • 5'-acylphosphoadenosine
  • Pentose-5-phosphate
  • Pentose phosphate
  • Lipoic_acid_derivative
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Acyl phosphate
  • Monosaccharide
  • Imidolactam
  • N-substituted imidazole
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Phosphoric acid ester
  • Azole
  • Dithiolane
  • Imidazole
  • Heteroaromatic compound
  • 1,2-dithiolane
  • Tetrahydrofuran
  • Organic disulfide
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxylic acid salt
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Primary amine
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic salt
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.12 g/LALOGPS
logP0.25ALOGPS
logP-2.3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area192.14 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity124.95 m³·mol⁻¹ChemAxon
Polarizability50.71 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Lipoic acid metabolismPW002499 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Lipoic acid metabolismec00785 Map00785
SMPDB Reactions
Lipoic acid + Adenosine triphosphate → Pyrophosphate + lipoyl-AMP
lipoyl-AMP + apoprotein → Protein N6-(lipoyl)lysine + Adenosine monophosphate
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ds-3913010000-e06df70a38935bfec6caJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03xs-9852448000-ab8656a944a15acff0d2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Lipoyl-AMP,1TMS,#1" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0911020000-403226dda50e9b19c782JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-09f2e5c022805e4e9fe4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-8cffaab609f0ad97292dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3779560000-3583b9a6776d5e619ce6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5911000000-bd5c472188d51d73ad0cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9500000000-b3956188225c40fb0715JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-97f9a62a74dc17a227c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9100360000-0957a91a14ca65d00ed6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u0-9200000000-598cbfd3e15d0060e791JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0101090000-158a5093458bb19523bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-55f0391000d477c8c77dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-c5661a88a8e2cb7260afJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID55451
HMDB IDHMDB0059635
Pubchem Compound ID23724672
Kegg IDC16238
ChemSpider ID26330628
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDLIPOYL-AMP

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.