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3-Hexaprenyl-4,5-dihydroxybenzoic acid (YMDB00460)

Identification
YMDB IDYMDB00460
Name3-Hexaprenyl-4,5-dihydroxybenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Hexaprenyl-4,5-Dihydroxybenzoic acid, also known as 3,4-dihydroxy-5-hexaprenylbenzoate or dhhpba, belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group. 3-Hexaprenyl-4,5-Dihydroxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-Hexaprenyl-4,5-Dihydroxybenzoate
  • 3-Hexaprenyl-4,5-Dihydroxybenzoic acid
  • 3,4-Dihydroxy-5-hexaprenylbenzoate
  • 3,4-Dihydroxy-5-hexaprenylbenzoic acid
  • Dhhpba
CAS number63975-40-6
WeightAverage: 562.8223
Monoisotopic: 562.402210216
InChI KeyVEPICJBQCOUQPI-IRVXXIIISA-N
InChIInChI=1S/C37H54O4/c1-27(2)13-8-14-28(3)15-9-16-29(4)17-10-18-30(5)19-11-20-31(6)21-12-22-32(7)23-24-33-25-34(37(40)41)26-35(38)36(33)39/h13,15,17,19,21,23,25-26,38-39H,8-12,14,16,18,20,22,24H2,1-7H3,(H,40,41)/b28-15+,29-17+,30-19+,31-21+,32-23+
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4,5-dihydroxybenzoic acid
Traditional IUPAC Namedhhpba
Chemical FormulaC37H54O4
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylbenzene-1,2-diols
Alternative Parents
Substituents
  • Polyprenylbenzene-1,2-diol
  • Sesterterpenoid
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP8.41ALOGPS
logP11.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity180.53 m³·mol⁻¹ChemAxon
Polarizability70.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
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
S-Adenosyl-L-methionine + 3-Hexaprenyl-4,5-dihydroxybenzoic acid → S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
KEGG Reactions
oxygen + 3-Hexaprenyl-4-hydroxybenzoic acid → 3-Hexaprenyl-4,5-dihydroxybenzoic acid
3-Hexaprenyl-4,5-dihydroxybenzoic acid + S-Adenosylmethionine → S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-3394440000-9ca4e15a8864fbc5776dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-5375429000-ea197f75d2ee1687f247JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TMS,#1" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0212090000-04095cbd227edc49a7a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0849150000-639873a7488c1a696007JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tb-1769200000-4cbbd0cfab58c6dd3764JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-a08e91d9fefaf0f162ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0000090000-99d552c5bbb95acff7ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfs-1702690000-7f58130fe1eabd49d71cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-ab699c4e48dd66694a10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02mi-0801190000-5746ee5667f6804445e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdk-2903720000-6606158339c54cc426d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1102690000-f4b5588e3e3d17d76262JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-1319400000-aa11a41d3c2156681370JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-0898400000-2eab6c20b158a56bdbf7JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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 ID18081
HMDB IDHMDB01063
Pubchem Compound ID194172
Kegg IDC05200
ChemSpider ID4444330
FOODB IDFDB022402
Wikipedia IDNot Available
BioCyc ID3-HEXAPRENYL-45-DIHYDROXYBENZOATE

Enzymes

Protein Details
1. Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial
General function:
Involved in methyltransferase activity
Specific function:
Non-specific O-methyltransferase that catalyzes the 2 O- methylation steps in the ubiquinone biosynthetic pathway
Gene Name:
COQ3
Uniprot ID:
P27680
Molecular weight:
36330.60156
Reactions
S-adenosyl-L-methionine + 3,4-dihydroxy-5-all-trans-polyprenylbenzoate → S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate.
S-adenosyl-L-methionine + 3-demethylubiquinone-n → S-adenosyl-L-homocysteine + ubiquinone-n.
S-adenosyl-L-methionine + 2-hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol → S-adenosyl-L-homocysteine + ubiquinol.
Protein Details
2. 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