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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Methylglutaconyl-CoA (HMDB01057)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:48 -0700
HMDB ID HMDB01057
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Methylglutaconyl-CoA
Description 3-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Methylglutaconyl-CoA
  2. 3-Methylglutaconyl-Coenzyme A
  3. trans-3-Methylglutaconyl-CoA
  4. trans-3-Methylglutaconyl-Coenzyme A
Chemical Formula C27H42N7O19P3S
Average Molecular Weight 893.644
Monoisotopic Molecular Weight 893.146902423
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 Number 6247-73-0
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 Key GXKSHRDAHFLWPN-NTEUORMPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl 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 Parent Acyl CoAs
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.24 g/L ALOGPS
LogP -0.43 ALOGPS
LogP -6.2 ChemAxon
LogS -2.44 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 5.01 ChemAxon
Hydrogen Acceptor Count 19 ChemAxon
Hydrogen Donor Count 10 ChemAxon
Polar Surface Area 400.93 A2 ChemAxon
Rotatable Bond Count 23 ChemAxon
Refractivity 193.08 ChemAxon
Polarizability 78.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -5 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Valine, Leucine and Isoleucine Degradation SMP00032 map00280 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022396
KNApSAcK ID Not Available
Chemspider ID 11471767 Link_out
KEGG Compound ID C03231 Link_out
BioCyc ID TRANS-3-METHYL-GLUTACONYL-COA Link_out
BiGG ID 41450 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01057 Link_out
Metagene Link HMDB01057 Link_out
METLIN ID 5971 Link_out
PubChem Compound 5462214 Link_out
PDB ID Not Available
ChEBI ID 15488 Link_out
References
Synthesis Reference Hermans-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 References Not Available
Enzymes
Name: Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial
Reactions:
  • ATP + 3-methylcrotonoyl-CoA + HCO3- = ADP + phosphate + 3-methylglutaconyl-CoA [RN:R04138]
Gene Name: MCCC2
Uniprot ID: Q9HCC0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial
Reactions:
  • ATP + 3-methylcrotonoyl-CoA + HCO3- = ADP + phosphate + 3-methylglutaconyl-CoA [RN:R04138]
Gene Name: MCCC1
Uniprot ID: Q96RQ3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylglutaconyl-CoA hydratase, mitochondrial
Reactions:
  • (S)-3-hydroxy-3-methylglutaryl-CoA = trans-3-methylglutaconyl-CoA + H2O [RN:R02085]
Gene Name: AUH
Uniprot ID: Q13825 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA