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2-Hexaprenyl-6-methoxy-1,4-benzoquinone (YMDB00174)

Identification
YMDB IDYMDB00174
Name2-Hexaprenyl-6-methoxy-1,4-benzoquinone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Hexaprenyl-6-methoxy-1,4-benzoquinone, also known as DDMQH2, 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 an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-polyprenyl-6-methoxy-1,4-benzoquinol
  • DDMQH2
CAS numberNot Available
WeightAverage: 546.8229
Monoisotopic: 546.407295594
InChI KeySCPRZSDIZDIQOW-FRICUITQSA-N
InChIInChI=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+
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 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
Chemical FormulaC37H54O3
SMILES[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C(=C([H])C([H])([H])C([H])([H])C(=C([H])C([H])([H])C([H])([H])C(=C([H])C([H])([H])C([H])([H])C(=C([H])C([H])([H])C([H])([H])C(=C([H])C([H])([H])C1=C([H])C(=O)C([H])=C(OC([H])([H])[H])C1=O)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Ubiquinone BiosynthesisPW002473 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB Reactions
2-hexaprenyl-6-methoxyphenol + oxygen → 2-Hexaprenyl-6-methoxy-1,4-benzoquinone + water
2-Hexaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosyl-L-methionine → 2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone + S-Adenosylhomocysteine
KEGG Reactions
2-Hexaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → 2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone + S-Adenosylhomocysteine + hydron
oxygen + 2-hexaprenyl-6-methoxyphenol → water + 2-Hexaprenyl-6-methoxy-1,4-benzoquinone
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-2796760000-ce022e97d5e44ff9c901JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1122090000-ba2655d411b93ef8fbb5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0479520000-8e7c5aaeb9fd993e7e59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lj-5389820000-c681b8bdedfe3c9481bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-4487eac63a220f28941bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000190000-3901c58bd6201adcfdf1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-5210490000-9fa6e69a66925ea89c1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-4a273ac8f57867e9838eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0520190000-9fe652b8c050d974a794JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rl-1916140000-85bcbc9707e7e38066ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054n-4350980000-3dae66c6f27d735ff02dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3910100000-443d7964a5424b957451JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7o-9831100000-190357a500b5697e8dbbJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Marbois, B., Gin, P., Faull, K. F., Poon, W. W., Lee, P. T., Strahan, J., Shepherd, J. N., Clarke, C. F. (2005). "Coq3 and Coq4 define a polypeptide complex in yeast mitochondria for the biosynthesis of coenzyme Q." J Biol Chem 280:20231-20238.15792955
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27752
HMDB IDHMDB06818
Pubchem Compound ID958
Kegg IDC05803
ChemSpider ID4444375
FOODB IDFDB024098
Wikipedia IDNot Available
BioCyc ID2-HEXAPRENYL-6-METHOXY-14-BENZOQUINOL

Enzymes

Protein Details
1. Ubiquinone biosynthesis protein COQ4, mitochondrial
General function:
Involved in ubiquinone biosynthetic process
Specific function:
Component of the coenzyme Q biosynthetic pathway. May play a role in organizing a multi-subunit COQ enzyme complex required for coenzyme Q biosynthesis. Required for steady-state levels of COQ3, COQ4, COQ6, COQ7 and COQ9 polypeptides
Gene Name:
COQ4
Uniprot ID:
O13525
Molecular weight:
38626.80078
Protein Details
2. Ubiquinone biosynthesis methyltransferase COQ5, mitochondrial
General function:
Involved in methyltransferase activity
Specific function:
Converts DDMQH2 into DMQH2
Gene Name:
COQ5
Uniprot ID:
P49017
Molecular weight:
34684.19922
Reactions
S-adenosyl-L-methionine + 2-polyprenyl-6-methoxy-1,4-benzoquinol → S-adenosyl-L-homocysteine + 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol.