Showing metabocard for Glutaryl-CoA (BMDB0001339)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:22 UTC
Update Date2020-05-21 16:28:33 UTC
BMDB IDBMDB0001339
Secondary Accession Numbers
  • BMDB01339
Metabolite Identification
Common NameGlutaryl-CoA
DescriptionGlutaryl-CoA 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. Glutaryl-CoA is a very strong basic compound (based on its pKa).
Structure
Thumb
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 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.48ALOGPS
logP-5.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.84ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity187.7 m³·mol⁻¹ChemAxon
Polarizability78.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-00kr-0005009000-eb3a971b38526182c8acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0a4i-0269300000-b433e45be2e4ddb9b3ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-05n1-0009700000-d04f275432ce90be4c03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0a4l-0691000000-1c9c9dcd3392e14e12d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0f80-0009841000-c64bfcd1084f04509fc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-000i-0009000000-8ef4f57ae35ca24154acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-014r-0001920000-f105e4c7bcf62b49d748View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, negativesplash10-001i-0000100090-7e0c0d1ae140f9f6c57cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, negativesplash10-053r-0000920060-2e8ff86ba386000c087eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 100V, negativesplash10-0a6r-1211920000-b87d792a259c80a7b01dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 123V, negativesplash10-056r-9835710000-f9df91f65d08757ed109View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 146V, negativesplash10-004i-9512100000-6725b9c211e210ffa4f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 169V, negativesplash10-004i-9400000000-3b7b4c8aa8db05827423View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 200V, negativesplash10-004i-9300000000-a481ad1113e5856425adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 232V, negativesplash10-004i-9200000000-484261819d8fe28a06bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 278V, negativesplash10-004i-9100000000-1ced5b391be9b0f5176cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-001i-0001960370-e5f5990aef17b3100ae7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-00di-0190000000-0bdc30775338012cc42fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0a4i-0900000000-816bc86479bd970ceed6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-9b9c96863df04861fbeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-43f2e61c32509ed14b97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-4ff7fbc1bd490ad4c020View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-3911030350-425e74ceb7a0a4256402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-2901010010-f93605fcb2512efdd305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-74a35eb8b1b0810315e4View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Fibroblasts
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001339
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Glutaryl-CoA dehydrogenase, mitochondrial
General function:
Lipid transport and metabolism
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 (By similarity).
Gene Name:
GCDH
Uniprot ID:
Q2KHZ9
Molecular weight:
48472.0
Reactions
Glutaryl-CoA → Crotonoyl-CoA + Carbon dioxidedetails
Glutaryl-CoA + electron-transfer flavoprotein → Crotonoyl-CoA + Reduced electron-transfer flavoprotein + Carbon dioxidedetails
Enzyme Details
2. Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial
General function:
Energy production and conversion
Specific function:
Dihydrolipoamide succinyltransferase (E2) component of the 2-oxoglutarate dehydrogenase complex (By similarity). The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2) (By similarity). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A (By similarity).
Gene Name:
DLST
Uniprot ID:
P11179
Molecular weight:
48973.0
Reactions
Oxoadipic acid + Coenzyme A → Glutaryl-CoA + Carbon dioxidedetails
Enzyme Details
3. 2-oxoglutarate dehydrogenase, mitochondrial
General function:
Energy production and conversion
Specific function:
2-oxoglutarate dehydrogenase (E1) component of the 2-oxoglutarate dehydrogenase complex, which mediates the decarboxylation of alpha-ketoglutarate. The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A.
Gene Name:
OGDH
Uniprot ID:
Q148N0
Molecular weight:
115808.0
Reactions
Oxoadipic acid + Coenzyme A → Glutaryl-CoA + Carbon dioxidedetails
Enzyme Details
4. Dihydrolipoyl dehydrogenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
DLD
Uniprot ID:
F1N206
Molecular weight:
54187.0
Reactions
Oxoadipic acid + Coenzyme A → Glutaryl-CoA + Carbon dioxidedetails