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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 through its interaction with the enzyme lipoate-protein ligase a. In yeast, lipoyl-AMP is involved in the metabolic pathway called the lipoic acid metabolism pathway.
Structure
Thumb
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 triphosphatePyrophosphate + 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 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
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

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.