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2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone (YMDB00437)

Identification
YMDB IDYMDB00437
Name2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Hexaprenyl-3-methyl-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. Based on a literature review a significant number of articles have been published on 2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinone
CAS numberNot Available
WeightAverage: 560.8494
Monoisotopic: 560.422945658
InChI KeyRLVSEUWSBSQQOE-NSUIJKAQSA-N
InChIInChI=1S/C38H56O3/c1-28(2)15-10-16-29(3)17-11-18-30(4)19-12-20-31(5)21-13-22-32(6)23-14-24-33(7)25-26-35-34(8)36(39)27-37(41-9)38(35)40/h15,17,19,21,23,25,27H,10-14,16,18,20,22,24,26H2,1-9H3/b29-17+,30-19+,31-21+,32-23+,33-25+
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione
Chemical FormulaC38H56O3
SMILESCOC1=CC(=O)C(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
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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
logP8.47ALOGPS
logP10.92ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity184.68 m³·mol⁻¹ChemAxon
Polarizability70.85 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-methoxy-1,4-benzoquinone + S-Adenosyl-L-methionine → 2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone + S-Adenosylhomocysteine
2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone + oxygen + NADPH + hydron → 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + water
KEGG Reactions
2-Hexaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → 2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone + S-Adenosylhomocysteine + hydron
NADH + 2-hexaprenyl-6-methoxy-3-methyl-1,4-benzoquinone + hydron + oxygen → NAD + water + 2-hexaprenyl-5-hydroxy-6-methoxy-3-methyl-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, Positivesplash10-0595-2395860000-076f0b0a5f3ac183d344JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0212190000-60a2d3b19eafb56e7298JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mp-0659320000-068d65be59f974e41f20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-4135910000-0ce81a43c47d598a8fd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-e3d37775d3f610720f29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1100290000-ae3b95d1846ca94e6136JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ox-9100680000-4d0ca8b1a7ef24062007JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-710d952b696f7a975ea5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0720290000-e03d87ca599eff19d01aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-1952220000-807c3decfe3ed0edee77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-5256790000-82a2fad27d17467962f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ls-9655210000-cf192b100b3e0d4d332aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9521000000-f52688303b6449cc1ee5JSpectraViewer
References
References:
  • 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 ID28711
HMDB IDHMDB0006819
Pubchem Compound ID351185
Kegg IDC05804
ChemSpider ID4444376
FOODB IDFDB024099
Wikipedia IDNot Available
BioCyc IDNot Available

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