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Showing metabocard for Glutaryl-CoA (HMDB0001339)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
enzymes (5) Show 5 proteins
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:13 UTC
HMDB IDHMDB0001339
Secondary Accession Numbers
  • HMDB01339
Metabolite Identification
Common NameGlutaryl-CoA
DescriptionGlutaryl-CoA is a substrate for 2-oxoglutarate dehydrogenase E1 component (mitochondrial), Dihydrolipoyllysine-residue succinyltransferase component of 2- oxoglutarate dehydrogenase complex (mitochondrial) and Glutaryl-CoA dehydrogenase (mitochondrial).
Structure
Data?1582752193
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Glutaryl-coenzyme AHMDB
Chemical FormulaC26H42N7O19P3S
Average Molecular Weight881.633
Monoisotopic Molecular Weight881.146902423
IUPAC Name5-{[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 Name5-({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
CAS Registry Number103192-48-9
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
InChI Identifier
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
InChI KeySYKWLIJQEHRDNH-KRPIADGTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2,3,4-saturated fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid
  • Carboxamide group
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Sulfenyl compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Carbonyl group
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility3.62 g/LALOGPS
logP-0.48ALOGPS
logP-6.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity187.7 m³·mol⁻¹ChemAxon
Polarizability78.02 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-9b9c96863df04861fbeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-43f2e61c32509ed14b97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-4ff7fbc1bd490ad4c020Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-3911030350-425e74ceb7a0a4256402Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-2901010010-f93605fcb2512efdd305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-74a35eb8b1b0810315e4Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Feces
Tissue Locations
  • Fibroblasts
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022563
KNApSAcK IDNot Available
Chemspider ID388388
KEGG Compound IDC00527
BioCyc IDNot Available
BiGG ID35255
Wikipedia LinkGlutaryl-CoA
METLIN ID6173
PubChem Compound439252
PDB IDNot Available
ChEBI ID15524
Food Biomarker OntologyNot Available
VMH IDGLUTCOA
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]

Enzymes

Enzyme Details
1. Dihydrolipoyl dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:
DLD
Uniprot ID:
P09622
Molecular weight:
54176.91
Enzyme Details
2. Glutaryl-CoA dehydrogenase, mitochondrial
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the oxidative decarboxylation of glutaryl-CoA to crotonyl-CoA and CO(2) in the degradative pathway of L-lysine, L-hydroxylysine, and L-tryptophan metabolism. It uses electron transfer flavoprotein as its electron acceptor. Isoform Short is inactive.
Gene Name:
GCDH
Uniprot ID:
Q92947
Molecular weight:
48126.715
Reactions
Glutaryl-CoA + electron-transfer flavoprotein → (E)-but-2-enoyl-CoA + CO(2) + reduced electron-transfer flavoproteindetails
Glutaryl-CoA + FAD → FADH + (E)-but-2-enoyl-CoA + Carbon dioxidedetails
Glutaryl-CoA + Electron-transferring flavoprotein → (E)-but-2-enoyl-CoA + Reduced electron-transferring flavoprotein + Carbon dioxidedetails
Glutaryl-CoA + Electron-transferring flavoprotein → Glutaconyl-CoA + Reduced electron-transferring flavoproteindetails
Enzyme Details
3. 2-oxoglutarate dehydrogenase, mitochondrial
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
OGDH
Uniprot ID:
Q02218
Molecular weight:
48179.59
Reactions
Oxoadipic acid + Coenzyme A + NAD → Glutaryl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails
Enzyme Details
4. Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial
General function:
Involved in acyltransferase activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
DLST
Uniprot ID:
P36957
Molecular weight:
48754.87
Reactions
Glutaryl-CoA + Enzyme N6-(dihydrolipoyl)lysine → Coenzyme A + [Dihydrolipoyllysine-residue succinyltransferase] S-glutaryldihydrolipoyllysinedetails
Enzyme Details
5. 2-oxoglutarate dehydrogenase-like, mitochondrial
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
Not Available
Gene Name:
OGDHL
Uniprot ID:
Q9ULD0
Molecular weight:
Not Available
Reactions
Oxoadipic acid + Coenzyme A + NAD → Glutaryl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails