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3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid (YMDB00461)

Identification
YMDB IDYMDB00461
Name3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group. Based on a literature review a significant number of articles have been published on 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-Hexaprenyl-4-hydroxy-5-methoxybenzoate
  • 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
  • 3-Methoxy-4-hydroxy-5-hexaprenylbenzoate
  • 3-Methoxy-4-hydroxy-5-hexaprenylbenzoic acid
  • 3-Mhhb
  • Hexaprenyl-4-hydroxy-5-methoxybenzoate
  • Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
CAS number66551-60-8
WeightAverage: 576.8488
Monoisotopic: 576.41786028
InChI KeyYSZSVGFMAJXGMQ-FRICUITQSA-N
InChIInChI=1S/C38H56O4/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(40)41)27-36(42-8)37(34)39/h14,16,18,20,22,24,26-27,39H,9-13,15,17,19,21,23,25H2,1-8H3,(H,40,41)/b29-16+,30-18+,31-20+,32-22+,33-24+
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxy-5-methoxybenzoic acid
Traditional IUPAC Name3-mhhb
Chemical FormulaC38H56O4
SMILESCOC1=C(O)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)=CC(=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Sesterterpenoid
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Methoxybenzene
  • Benzoyl
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen 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
logP8.61ALOGPS
logP11.2ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity185.01 m³·mol⁻¹ChemAxon
Polarizability72.35 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
S-Adenosyl-L-methionine + 3-Hexaprenyl-4,5-dihydroxybenzoic acid → S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
KEGG Reactions
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid + hydron → Carbon dioxide + 2-hexaprenyl-6-methoxyphenol
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, Positivesplash10-08g0-2388590000-89e434c77e88e9089ef4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003r-3147469000-0708567822e5bfd90a9eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3-Hexaprenyl-4-hydroxy-5-methoxybenzoic 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_2_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_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0212090000-055eaf6bf9bb7f66403fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003s-0739160000-67aa4818a2ec38ef35ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gxt-1359210000-0d48ce3c1daca56ef467JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-a22409cb6dbbb1a464f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0000090000-dda0834068a4ec0b05d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-2200290000-211ab1bf8b89830eeb7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-37874bf3cdf6a781a33eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0300090000-a09c79ecaeb909c9402bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0856590000-a0df803dc315dc2ff708JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05e9-2011390000-7b7b6746ebaefb787192JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-5925200000-1bbeb139fd4f40c1b6c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-9632000000-60f2ecc1d8003b07f78cJSpectraViewer
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 ID16835
HMDB IDHMDB00977
Pubchem Compound ID6443832
Kegg IDC05313
ChemSpider ID4444339
FOODB IDFDB022347
Wikipedia IDNot Available
BioCyc ID3-HEXAPRENYL-4-HYDROXY-5-METHOXYBENZOATE

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