Showing metabocard for 2-Hexaprenyl-6-methoxy-1,4-benzoquinone (BMDB0006818)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:22 UTC
Update Date2020-05-21 16:28:36 UTC
BMDB IDBMDB0006818
Secondary Accession Numbers
  • BMDB06818
Metabolite Identification
Common Name2-Hexaprenyl-6-methoxy-1,4-benzoquinone
Description2-Hexaprenyl-6-methoxy-1,4-benzoquinone belongs to the class of organic compounds known as polyprenylbenzoquinones. Polyprenylbenzoquinones are compounds containing a polyisoprene chain attached to a quinone at the second ring position. 2-Hexaprenyl-6-methoxy-1,4-benzoquinone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Hexaprenyl-6-methoxy-1,4-benzoquinone exists in all eukaryotes, ranging from yeast to humans. In cattle, 2-hexaprenyl-6-methoxy-1,4-benzoquinone is involved in the metabolic pathway called ubiquinone biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Polyprenyl-6-methoxy-1,4-benzoquinolHMDB
DDMQH2HMDB
Chemical FormulaC37H54O3
Average Molecular Weight546.8229
Monoisotopic Molecular Weight546.407295594
IUPAC Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione
Traditional Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)C=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1=O
InChI Identifier
InChI=1S/C37H54O3/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-26-35(38)27-36(40-8)37(34)39/h14,16,18,20,22,24,26-27H,9-13,15,17,19,21,23,25H2,1-8H3/b29-16+,30-18+,31-20+,32-22+,33-24+
InChI KeySCPRZSDIZDIQOW-FRICUITQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylbenzoquinones. Polyprenylbenzoquinones are compounds containing a polyisoprene chain attached to a quinone at the second ring position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPolyprenylbenzoquinones
Alternative Parents
Substituents
  • Polyprenylbenzoquinone
  • Sesterterpenoid
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.41ALOGPS
logP10.53ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity180.32 m³·mol⁻¹ChemAxon
Polarizability69.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-2796760000-ce022e97d5e44ff9c901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1122090000-ba2655d411b93ef8fbb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0479520000-8e7c5aaeb9fd993e7e59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lj-5389820000-c681b8bdedfe3c9481bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-4487eac63a220f28941bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000190000-3901c58bd6201adcfdf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-5210490000-9fa6e69a66925ea89c1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-4a273ac8f57867e9838eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0520190000-9fe652b8c050d974a794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rl-1916140000-85bcbc9707e7e38066ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054n-4350980000-3dae66c6f27d735ff02dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3910100000-443d7964a5424b957451View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7o-9831100000-190357a500b5697e8dbbView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006818
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024098
KNApSAcK IDNot Available
Chemspider ID4444375
KEGG Compound IDC05803
BioCyc IDCPD-11655
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280826
PDB IDNot Available
ChEBI ID27752
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial
General function:
Coenzyme transport and metabolism
Specific function:
Methyltransferase required for the conversion of 2-polyprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) to 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2).
Gene Name:
COQ5
Uniprot ID:
Q0P5A2
Molecular weight:
37591.0
Reactions
2-Hexaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → 2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone + S-Adenosylhomocysteinedetails
Enzyme Details
2. Ubiquinone biosynthesis monooxygenase COQ6, mitochondrial
General function:
Coenzyme transport and metabolism
Specific function:
FAD-dependent monooxygenase required for the C5-ring hydroxylation during ubiquinone biosynthesis. Catalyzes the hydroxylation of 3-polyprenyl-4-hydroxybenzoic acid to 3-polyprenyl-4,5-dihydroxybenzoic acid. The electrons required for the hydroxylation reaction may be funneled indirectly from NADPH via a ferredoxin/ferredoxin reductase system to COQ6.
Gene Name:
COQ6
Uniprot ID:
Q2KIL4
Molecular weight:
51072.0
Reactions
2-Hexaprenyl-6-methoxyphenol + Oxygen → 2-Hexaprenyl-6-methoxy-1,4-benzoquinone + Waterdetails