| Record Information |
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| Version | 4.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2010-05-13 16:18:27 UTC |
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| Update Date | 2020-02-26 21:38:57 UTC |
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| HMDB ID | HMDB0013617 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Lipoyl-GMP |
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| Description | Lipoyl-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. |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C18H26N5O9PS2 |
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| Average Molecular Weight | 551.531 |
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| Monoisotopic Molecular Weight | 551.090955347 |
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| 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 |
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| 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 |
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| CAS Registry Number | Not Available |
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| 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 |
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| 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 |
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| InChI Key | DVZGUOFXTLKZTJ-LQLSJNDNSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. |
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| Kingdom | Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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| Class | Purine nucleotides |
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| Sub Class | Purine ribonucleotides |
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| Direct Parent | Purine ribonucleoside monophosphates |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Source: |
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| Process | Naturally occurring process: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-9604120000-de816c9fb2bd0d3c1b46 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-000t-9500043000-a30932f85928bf71d92e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udl-0519030000-754089a9fa43bda9e003 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udl-1945000000-e75c3e62d91aded13ca1 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0935000000-a51ba7fe44663f6e05a0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ug0-5115390000-8320344335a6fea019d3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9225000000-3cfe2164ffad44730975 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-bbfe4770f80179106df6 | Spectrum |
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