Showing metabocard for 3-Methylglutaconyl-CoA (BMDB0001057)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:29 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0001057
Secondary Accession Numbers
  • BMDB01057
Metabolite Identification
Common Name3-Methylglutaconyl-CoA
Description3-Methylglutaconyl-CoA belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, 3-methylglutaconyl-CoA is considered to be a fatty ester lipid molecule. 3-Methylglutaconyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Methylglutaconyl-coenzyme AHMDB
trans-3-Methylglutaconyl-CoAHMDB
trans-3-Methylglutaconyl-coenzyme AHMDB
Chemical FormulaC27H42N7O19P3S
Average Molecular Weight893.644
Monoisotopic Molecular Weight893.146902423
IUPAC Name(3E)-5-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-3-methyl-5-oxopent-3-enoic acid
Traditional Name(3E)-5-[(2-{[3-({4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene}amino)-1-hydroxypropylidene]amino}ethyl)sulfanyl]-3-methyl-5-oxopent-3-enoic acid
CAS Registry Number6247-73-0
SMILES
C\C(CC(O)=O)=C/C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C27H42N7O19P3S/c1-14(8-17(36)37)9-18(38)57-7-6-29-16(35)4-5-30-25(41)22(40)27(2,3)11-50-56(47,48)53-55(45,46)49-10-15-21(52-54(42,43)44)20(39)26(51-15)34-13-33-19-23(28)31-12-32-24(19)34/h9,12-13,15,20-22,26,39-40H,4-8,10-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b14-9+
InChI KeyGXKSHRDAHFLWPN-NTEUORMPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl 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
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-0.21ALOGPS
logP-3.5ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area407.91 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity194.12 m³·mol⁻¹ChemAxon
Polarizability79.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2922000140-ab8cfafbf82b69784d01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0924000000-289a60cd136a829694adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-948db20c213440c24333View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-3921140370-36127567b61b2109c1c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4910010000-dffb260ce4e016ee88bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-4900000000-b42ed3096bbd5bc2ac03View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001057
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022396
KNApSAcK IDNot Available
Chemspider ID11471767
KEGG Compound IDC03231
BioCyc IDNot Available
BiGG ID41450
Wikipedia Link3-Methylglutaconyl-CoA
METLIN ID5971
PubChem Compound5462214
PDB IDNot Available
ChEBI ID15488
References
Synthesis ReferenceHermans-Lokkerbol, Ank; van der Heijden, Robert; Verpoorte, Robert. Isocratic high-performance liquid chromatography of coenzyme A esters involved in the metabolism of 3S-hydroxy-3-methylglutaryl-coenzyme A. Detection of related enzyme activities in Catharanthus roseus plant cell cultures. Journal of Chromatography, A (1996), 752(1+2), 123-130.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Propionyl-CoA carboxylase beta chain, mitochondrial
General function:
Involved in ATP binding
Specific function:
This is one of the 2 subunits of the biotin-dependent propionyl-CoA carboxylase (PCC), a mitochondrial enzyme involved in the catabolism of odd chain fatty acids, branched-chain amino acids isoleucine, threonine, methionine, and valine and other metabolites. Propionyl-CoA carboxylase catalyzes the carboxylation of propionyl-CoA/propanoyl-CoA to D-methylmalonyl-CoA/(S)-methylmalonyl-CoA (By similarity). Within the holoenzyme, the alpha subunit catalyzes the ATP-dependent carboxylation of the biotin carried by the biotin carboxyl carrier (BCC) domain, while the beta subunit then transfers the carboxyl group from carboxylated biotin to propionyl-CoA (By similarity). Propionyl-CoA carboxylase also significantly acts on butyryl-CoA/butanoyl-CoA, which is converted to ethylmalonyl-CoA/(2S)-ethylmalonyl-CoA (By similarity). Other alternative minor substrates include (2E)-butenoyl-CoA/crotonoyl-CoA (By similarity).
Gene Name:
PCCB
Uniprot ID:
Q2TBR0
Molecular weight:
58311.0
Reactions
3-Methylcrotonyl-CoA + Adenosine triphosphate + Hydrogen carbonate → 3-Methylglutaconyl-CoA + ADPdetails
Enzyme Details
2. Pyruvate carboxylase, mitochondrial
General function:
Involved in ATP binding
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate (By similarity).
Gene Name:
PC
Uniprot ID:
Q29RK2
Molecular weight:
129698.0
Reactions
3-Methylcrotonyl-CoA + Adenosine triphosphate + Hydrogen carbonate → 3-Methylglutaconyl-CoA + ADPdetails
Enzyme Details
3. Enoyl-CoA hydratase domain-containing protein 2, mitochondrial
General function:
Not Available
Specific function:
Not Available
Gene Name:
ECHDC2
Uniprot ID:
Q2TBT3
Molecular weight:
31604.0
Reactions
3-Methylglutaconyl-CoA + Water → 3-Hydroxy-3-methylglutaryl-CoAdetails