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3-Hexaprenyl-4-hydroxybenzoic acid (YMDB00459)

Identification
YMDB IDYMDB00459
Name3-Hexaprenyl-4-hydroxybenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Hexaprenyl-4-hydroxybenzoic acid belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group. 3-Hexaprenyl-4-hydroxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (all-E)-3-(3,7,11,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoic acid
  • 3-Hexaprenyl-4-hydroxybenzoate
  • all-trans-3-(3,7,11,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoic acid
  • (all-e)-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoate
  • all-trans-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoate
  • 3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxy-benzoate
  • 3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxy-benzoic acid
CAS number65848-03-5
WeightAverage: 546.8229
Monoisotopic: 546.407295594
InChI KeyLKMQQQABIGIHGL-LAAQXVIISA-N
InChIInChI=1S/C37H54O3/c1-28(2)13-8-14-29(3)15-9-16-30(4)17-10-18-31(5)19-11-20-32(6)21-12-22-33(7)23-24-34-27-35(37(39)40)25-26-36(34)38/h13,15,17,19,21,23,25-27,38H,8-12,14,16,18,20,22,24H2,1-7H3,(H,39,40)/b29-15+,30-17+,31-19+,32-21+,33-23+
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxybenzoic acid
Traditional IUPAC Name3-hexaprenyl-4-hydroxybenzoate
Chemical FormulaC37H54O3
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C=CC(=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylphenols
Alternative Parents
Substituents
  • Polyprenylphenol
  • Sesterterpenoid
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • 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 Solubility0.00036 g/LALOGPS
logP8.74ALOGPS
logP11.35ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity178.55 m³·mol⁻¹ChemAxon
Polarizability68.67 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
4-Hydroxybenzoic acid + hexaprenyl diphosphate → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphate
KEGG Reactions
oxygen + 3-Hexaprenyl-4-hydroxybenzoic acid → 3-Hexaprenyl-4,5-dihydroxybenzoic acid
hexaprenyl diphosphate + 4-Hydroxybenzoic acid → Pyrophosphate + 3-Hexaprenyl-4-hydroxybenzoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ai-3496450000-5b468805ae29a5f59a42JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3222219000-0638b89fa0bde34d7abbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3-Hexaprenyl-4-hydroxybenzoic acid,1TMS,#1" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 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 (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_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-0111090000-0efba026d858a4ae0c57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0749360000-6112d4d11f00cf6a1fbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2579200000-1a695b7874053d38599aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-451426c2227e9a66c0aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0000190000-4173c10b0b5d3133deabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2112920000-b9b9e484d8dc60509991JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-1102590000-0baf32808b3ddee5f52bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uy0-1629600000-89c41d697dba8ac52603JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-0859510000-223193ff35c3e152d619JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-d1b5f9d61cd518fa226bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0900010000-73c408ecbea0457640caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1403900000-b753301bd29d4e9b1925JSpectraViewer
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID31116
HMDB IDHMDB06816
Pubchem Compound ID6438959
Kegg IDC13425
ChemSpider ID10128306
FOODB IDFDB030426
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Para-hydroxybenzoate--polyprenyltransferase, mitochondrial
General function:
Involved in prenyltransferase activity
Specific function:
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB
Gene Name:
COQ2
Uniprot ID:
P32378
Molecular weight:
41001.0
Reactions
A polyprenyl diphosphate + 4-hydroxybenzoate → diphosphate + a 4-hydroxy-3-polyprenylbenzoate.