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Record Information
Version	2.0
Creation Date	2012-05-31 13:50:14 -0600
Update Date	2015-06-03 15:53:56 -0600
Secondary Accession Numbers	ECMDB01339
Identification
Name:	Glutaryl-CoA
Description	Glutaryl-coenzyme A (or Glutaryl-CoA) is an intermediate in the metabolism of lysine and tryptophan.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa9e070a0> Close
Synonyms:	Glutaryl-CoA Glutaryl-coenzyme A
Chemical Formula:	C26H42N7O19P3S
Weight:	Average: 881.633 Monoisotopic: 881.146902423
InChI Key:	SYKWLIJQEHRDNH-KRPIADGTSA-N
InChI:	InChI=1S/C26H42N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h12-14,19-21,25,38-39H,3-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,19-,20-,21?,25-/m1/s1
CAS number:	103192-48-9
IUPAC Name:	5-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-oxopentanoic acid
Traditional IUPAC Name:	5-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-5-oxopentanoic acid
SMILES:	CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	Long-chain fatty acyl CoAs
Alternative Parents	2,3,4-saturated fatty acyl CoAs Coenzyme A and derivatives Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates Imidolactams N-acyl amines N-substituted imidazoles Heteroaromatic compounds Tetrahydrofurans Thioesters Secondary alcohols Carbothioic S-esters Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Sulfenyl compounds Organopnictogen compounds Hydrocarbon derivatives Primary amines Carbonyl compounds Organic oxides
Substituents	Coenzyme a or derivatives Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Ribonucleoside 3'-phosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Organic pyrophosphate Pentose monosaccharide Imidazopyrimidine Purine Monoalkyl phosphate Aminopyrimidine Imidolactam N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Monosaccharide Pyrimidine Alkyl phosphate Fatty amide Phosphoric acid ester Tetrahydrofuran Imidazole Azole Heteroaromatic compound Carbothioic s-ester Secondary alcohol Thiocarboxylic acid ester Carboxamide group Secondary carboxylic acid amide Amino acid or derivatives Sulfenyl compound Thiocarboxylic acid or derivatives Organoheterocyclic compound Azacycle Oxacycle Carboxylic acid derivative Organosulfur compound Organic oxygen compound Hydrocarbon derivative Carbonyl group Organic nitrogen compound Primary amine Organopnictogen compound Organic oxide Organooxygen compound Organonitrogen compound Alcohol Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Fatty acyl CoAs (C00154 )
Physical Properties
State:	Solid
Charge:	-5
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.62 g/L ALOGPS logP -0.48 ALOGPS logP -5.6 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 0.82 ChemAxon pKa (Strongest Basic) 3.84 ChemAxon Physiological Charge -5 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 400.93 Ų ChemAxon Rotatable Bond Count 24 ChemAxon Refractivity 187.7 m³·mol⁻¹ ChemAxon Polarizability 78.94 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Oxoadipic acid + Coenzyme A + NAD <> Glutaryl-CoA + Carbon dioxide + NADH + Hydrogen ion Glutaryl-CoA + Enzyme N6-(dihydrolipoyl)lysine <> Coenzyme A + [Dihydrolipoyllysine-residue succinyltransferase] S-glutaryldihydrolipoyllysine Glutaryl-CoA > Crotonoyl-CoA + Carbon dioxide Oxoadipic acid + Coenzyme A + NAD <> Glutaryl-CoA + Carbon dioxide + NADH + Hydrogen ion
SMPDB Pathways:	Fatty acid metabolism PW000796 Tryptophan metabolism PW000815
KEGG Pathways:	Benzoate degradation via hydroxylation ec00362 Fatty acid metabolism ec00071 Lysine degradation ec00310 Microbial metabolism in diverse environments ec01120 Tryptophan metabolism ec00380
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-00kr-0005009000-eb3a971b38526182c8ac View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-0a4i-0269300000-b433e45be2e4ddb9b3dd View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-05n1-0009700000-d04f275432ce90be4c03 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-0a4l-0691000000-1c9c9dcd3392e14e12d9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-0f80-0009841000-c64bfcd1084f04509fc5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-000i-0009000000-8ef4f57ae35ca24154ac View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-014r-0001920000-f105e4c7bcf62b49d748 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 61V, negative splash10-001i-0000100090-7e0c0d1ae140f9f6c57c View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 77V, negative splash10-053r-0000920060-2e8ff86ba386000c087e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 100V, negative splash10-0a6r-1211920000-b87d792a259c80a7b01d View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 123V, negative splash10-056r-9835710000-f9df91f65d08757ed109 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 146V, negative splash10-004i-9512100000-6725b9c211e210ffa4f9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 169V, negative splash10-004i-9400000000-3b7b4c8aa8db05827423 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 200V, negative splash10-004i-9300000000-a481ad1113e5856425ad View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 232V, negative splash10-004i-9200000000-484261819d8fe28a06bc View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 278V, negative splash10-004i-9100000000-1ced5b391be9b0f5176c View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-001i-0001960370-e5f5990aef17b3100ae7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-00di-0190000000-0bdc30775338012cc42f View in MoNA LC-MS/MS LC-MS/MS Spectrum - n/a 61V, negative splash10-0a4i-0900000000-816bc86479bd970ceed6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-1912000130-9b9c96863df04861fbee View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0913000000-43f2e61c32509ed14b97 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1901000000-4ff7fbc1bd490ad4c020 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01q9-3911030350-425e74ceb7a0a4256402 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01si-2901010010-f93605fcb2512efdd305 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900100000-74a35eb8b1b0810315e4 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Corral I, Martinez Castrillo JC, Martinez-Pardo M, Gimeno A: [Glutaric aciduria type I: diagnosis in adulthood and phenotypic variability] Neurologia. 2001 Oct;16(8):377-80. Pubmed: 11738016 Hyman DB, Tanaka K: Specific glutaryl-CoA dehydrogenating activity is deficient in cultured fibroblasts from glutaric aciduria patients. J Clin Invest. 1984 Mar;73(3):778-84. Pubmed: 6423663 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Mahfoud A, Dominguez CL, Rizzo C, Ribes A: [In utero macrocephaly as clinical manifestation of glutaric aciduria type I. Report of a novel mutation] Rev Neurol. 2004 Nov 16-30;39(10):939-42. Pubmed: 15573311
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15524 HMDB ID HMDB01339 Pubchem Compound ID 439252 Kegg ID C00527 ChemSpider ID 388388 Wikipedia Glutaryl-CoA BioCyc ID GLUTARYL-COA EcoCyc ID GLUTARYL-COA

Enzymes