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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2010-05-13 16:18:27 UTC
Update Date2017-10-23 19:06:12 UTC
HMDB IDHMDB0013617
Secondary Accession Numbers
  • HMDB13617
Metabolite Identification
Common NameLipoyl-GMP
DescriptionLipoyl-GMP is an intermediate in lipoic acid metabolism.In mammals, the posttranslational modification of unlipoylated apoproteins by addition of lipoic acid is done in a two-step enzymatic reaction using free lipoic acid. The free lipoic acid in the cell is first activated by reacting it. with adenosine triphosphate, using up two high energy phosphate bonds to form lipoyl-AMP (GMP), a process catalyzed by lipoate activating enzyme (LAE).41 The activated lipoyl moiety is subsequently used to form an amide bond with lysine residues of the unlipoylated apoprotein, which is catalyzed by lipoyl-AMP(GMP):N-lysine lipoyl transferase Interestingly, purified LAE from bovine liver mitochondria preferentially utilizes guanosine triphosphate, instead of adenosine triphosphate, for the activation of lipoic acid to form lipoyl-GMP.44 Furthermore, genetic analysis of LAE reveals that the enzyme is identical to. xenobiotic-metabolizing/medium-chain fatty acid:CoA ligase-III (XL-III) (also from bovine liver mitochondria). 44 Hence, there appear to be two pathways in which LAE is capable of activating carboxylic acids: one that uses guanosine triphosphate to form acyl-GMP; the other is dependent on adenosine triphosphate for the activation of carboxylic acids to the CoA thioester (acyl-CoA) via an. acyl-AMP intermediate.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H26N5O9PS2
Average Molecular Weight551.531
Monoisotopic Molecular Weight551.090955347
IUPAC Name{[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC(=O)CCCCC1CCSS1)NC2=O
InChI Identifier
InChI=1S/C18H26N5O9PS2/c24-11(4-2-1-3-9-5-6-34-35-9)20-18-21-15-12(16(27)22-18)19-8-23(15)17-14(26)13(25)10(32-17)7-31-33(28,29)30/h8-10,13-14,17,25-26H,1-7H2,(H2,28,29,30)(H2,20,21,22,24,27)/t9?,10-,13-,14-,17-/m1/s1
InChI KeyDVZGUOFXTLKZTJ-LQLSJNDNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Lipoamide
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • N-arylamide
  • Monoalkyl phosphate
  • Pyrimidone
  • Fatty acyl
  • Fatty amide
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • 1,2-dithiolane
  • Heteroaromatic compound
  • Dithiolane
  • Imidazole
  • Vinylogous amide
  • Azole
  • Secondary alcohol
  • Organic disulfide
  • Secondary carboxylic acid amide
  • 1,2-diol
  • Carboxamide group
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.12 g/LALOGPS
logP0.55ALOGPS
logP-0.86ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)0.37ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area204.83 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity126.67 m³·mol⁻¹ChemAxon
Polarizability52.23 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9604120000-de816c9fb2bd0d3c1b46View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000t-9500043000-a30932f85928bf71d92eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udl-0519030000-754089a9fa43bda9e003View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-1945000000-e75c3e62d91aded13ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0935000000-a51ba7fe44663f6e05a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug0-5115390000-8320344335a6fea019d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9225000000-3cfe2164ffad44730975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-bbfe4770f80179106df6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyPw000061Pw000061 greyscalePw000061 simpleNot Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyPw000063Pw000063 greyscalePw000063 simpleNot Available
3-Methylcrotonyl Coa Carboxylase Deficiency Type IPw000065Pw000065 greyscalePw000065 simpleNot Available
3-Methylglutaconic Aciduria Type IPw000066Pw000066 greyscalePw000066 simpleNot Available
3-Methylglutaconic Aciduria Type IIIPw000067Pw000067 greyscalePw000067 simpleNot Available
Displaying entries 1 - 5 of 17 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029596
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481910
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ACSM6
Uniprot ID:
Q6P461
Molecular weight:
53584.545