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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0001290
Secondary Accession Numbers
  • HMDB01290
Metabolite Identification
Common NameGlutaconyl-CoA
DescriptionGlutaconyl-CoA (CAS: 6712-05-6), also known as 4-carboxybut-2-enoyl-CoA, belongs to the class of organic compounds known as 2-enoyl CoAs. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Thus, glutaconyl-CoA is considered to be a fatty ester lipid molecule. Glutaconyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Glutaconyl-CoA is a substrate for glutaryl-CoA dehydrogenase.
Structure
Data?1588782759
Synonyms
ValueSource
4-Carboxybut-2-enoyl-CoAChEBI
Glutaconyl-1-CoAChEBI
Glutaconyl-CoAKegg
(e)-Glutaconyl-CoAKegg
(2E)-4-Carboxybut-2-enoyl-CoAKegg
Glutaconyl-coenzyme AMeSH
Glutaconyl CoAHMDB
Glutaconyl coenzyme AHMDB
trans-Glutaconyl CoAHMDB
trans-Glutaconyl coenzyme AHMDB
trans-Glutaconyl-CoAHMDB
trans-Glutaconyl-coenzyme AHMDB
Chemical FormulaC26H40N7O19P3S
Average Molecular Weight879.62
Monoisotopic Molecular Weight879.131254264
IUPAC Name(3E)-5-[(2-{3-[(2R)-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-oxopent-3-enoic acid
Traditional Nameglutaconyl-1-coa
CAS Registry Number167357-83-7
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@@H](O)C(=O)NCCC(=O)NCCSC(=O)\C=C\CC(O)=O
InChI Identifier
InChI=1S/C26H40N7O19P3S/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/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/b5-3+/t14-,19-,20-,21+,25-/m1/s1
InChI KeyURTLOTISFJPPOU-DEGQQWIJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2-enoyl 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility3.24 g/LALOGPS
logP-0.35ALOGPS
logP-5.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.8ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity188.8 m³·mol⁻¹ChemAxon
Polarizability78.44 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-bad2528f55845486ec97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-f1770c613e8d38445e6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-24705b108f44454f66abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02e9-2911030450-5345dae7983df2f713f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910010000-f867f63c8922e78ed5e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-4900100000-bb243f20c4fb43f224d4Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022535
KNApSAcK IDNot Available
Chemspider ID7822023
KEGG Compound IDC02411
BioCyc IDGLUTACONYL-COA
BiGG IDNot Available
Wikipedia LinkGlutaconyl-CoA
METLIN IDNot Available
PubChem Compound9543050
PDB IDNot Available
ChEBI ID15497
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lehnert W, Sass JO: Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I). Med Hypotheses. 2005;65(2):330-3. [PubMed:15922108 ]

Only showing the first 10 proteins. There are 112 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Molecular weight:
57839.31
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADL
Uniprot ID:
P28330
Molecular weight:
47655.275
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADS
Uniprot ID:
P16219
Molecular weight:
44296.705
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:
ACADM
Uniprot ID:
P11310
Molecular weight:
46587.98
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:
ACOX1
Uniprot ID:
Q15067
Molecular weight:
70135.205
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:
ACOX2
Uniprot ID:
Q99424
Molecular weight:
76826.14
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
IVD
Uniprot ID:
P26440
Molecular weight:
43055.325

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5

Only showing the first 10 proteins. There are 112 proteins in total.