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nonaprenyl 4-hydroxybenzoate (YMDB00615)

Identification
YMDB IDYMDB00615
Namenonaprenyl 4-hydroxybenzoate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionnonaprenyl 4-hydroxybenzoate belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units. nonaprenyl 4-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-Nonaprenyl-4-hydroxybenzoate
  • Nonaprenyl-4-hydroxybenzoate
  • Nonaprenyl-4-hydroxybenzoic acid
  • Nonaprenyl 4-hydroxybenzoic acid
CAS numberNot Available
WeightAverage: 751.1739
Monoisotopic: 750.595096362
InChI KeyYIXNPXUQGCNFPX-RTPSYSNVSA-N
InChIInChI=1S/C52H78O3/c1-41(2)19-11-20-42(3)21-12-22-43(4)23-13-24-44(5)25-14-26-45(6)27-15-28-46(7)29-16-30-47(8)31-17-32-48(9)33-18-34-49(10)39-40-55-52(54)50-35-37-51(53)38-36-50/h19,21,23,25,27,29,31,33,35-39,53H,11-18,20,22,24,26,28,30,32,34,40H2,1-10H3/b42-21+,43-23+,44-25+,45-27+,46-29+,47-31+,48-33+,49-39+
IUPAC Name(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl 4-hydroxybenzoate
Traditional IUPAC Namenonaprenyl 4-hydroxybenzoate
Chemical FormulaC52H78O3
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COC(=O)C1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyterpenoids
Direct ParentPolyterpenoids
Alternative Parents
Substituents
  • Polyterpenoid
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP10.04ALOGPS
logP16.31ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity249.6 m³·mol⁻¹ChemAxon
Polarizability98.36 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG Reactions
nonaprenyl diphosphate + 4-Hydroxybenzoic acid ↔ Pyrophosphate + hydron + nonaprenyl 4-hydroxybenzoate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ir9-0712156900-f565998d903a97da6ceaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0512339000-c768166ce802a0fa9f73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1934463000-ab7c4257a84c6dfdecf4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1400002900-c91d0765c6ad92218382JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-3900001100-054ab730499d8c8c2a15JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-9700031000-002d642a948151bfce16JSpectraViewer
References
References:
  • 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
  • He, B., Chen, P., Chen, S. Y., Vancura, K. L., Michaelis, S., Powers, S. (1991). "RAM2, an essential gene of yeast, and RAM1 encode the two polypeptide components of the farnesyltransferase that prenylates a-factor and Ras proteins." Proc Natl Acad Sci U S A 88:11373-11377.1763050
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18162
HMDB IDNot Available
Pubchem Compound ID5280630
Kegg IDC03885
ChemSpider ID24808132
FOODB IDNot Available
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.
Protein Details
2. Protein farnesyltransferase subunit beta
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a farnesyl moiety from farnesyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins such as a-factor and RAS. The beta subunit is responsible for peptide-binding
Gene Name:
RAM1
Uniprot ID:
P22007
Molecular weight:
48189.39844
Reactions
Farnesyl diphosphate + protein-cysteine → S-farnesyl protein + diphosphate.