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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:48 UTC
HMDB IDHMDB01057
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methylglutaconyl-CoA
Description3-Methylglutaconyl-CoA is a substrate for Methylglutaconyl-CoA hydratase (mitochondrial), Methylcrotonoyl-CoA carboxylase beta chain (mitochondrial) and Methylcrotonoyl-CoA carboxylase alpha chain (mitochondrial).
Structure
Thumb
Synonyms
  1. 3-Methylglutaconyl-CoA
  2. 3-Methylglutaconyl-Coenzyme A
  3. trans-3-Methylglutaconyl-CoA
  4. trans-3-Methylglutaconyl-Coenzyme A
Chemical FormulaC27H42N7O19P3S
Average Molecular Weight893.644
Monoisotopic Molecular Weight893.146902423
IUPAC Name(3E)-5-{[2-(3-{3-[({[({[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}-3-methyl-5-oxopent-3-enoic acid
Traditional IUPAC Name(3E)-5-({2-[3-(3-{[({[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)-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
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Acid
  • Carboxylic Thioester
  • Coenzyme A
  • Enone
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Isoprene
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct ParentAcyl CoAs
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
Water Solubility3.24 g/LALOGPS
logP-0.43ALOGPS
logP-6.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity193.08ChemAxon
Polarizability78.92ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032map00280
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022396
KNApSAcK IDNot Available
Chemspider ID11471767
KEGG Compound IDC03231
BioCyc IDTRANS-3-METHYL-GLUTACONYL-COA
BiGG ID41450
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01057
Metagene LinkHMDB01057
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

General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
MCCC2
Uniprot ID:
Q9HCC0
Molecular weight:
61332.65
Reactions
Adenosine triphosphate + 3-Methylcrotonyl-CoA + Carbonic acid → ADP + Phosphoric acid + 3-Methylglutaconyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MCCC1
Uniprot ID:
Q96RQ3
Molecular weight:
80472.45
Reactions
Adenosine triphosphate + 3-Methylcrotonyl-CoA + Carbonic acid → ADP + Phosphoric acid + 3-Methylglutaconyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of 3-methylglutaconyl-CoA to 3-hydroxy-3-methylglutaryl-CoA. Has very low enoyl-CoA hydratase activity. Was originally identified as RNA-binding protein that binds in vitro to clustered 5'-AUUUA-3' motifs.
Gene Name:
AUH
Uniprot ID:
Q13825
Molecular weight:
35608.18
Reactions
3-Hydroxy-3-methylglutaryl-CoA → 3-Methylglutaconyl-CoA + Waterdetails
3-Hydroxy-3-methylglutaryl-CoA → 3-Methylglutaconyl-CoA + Waterdetails