all-trans-nonaprenyl diphosphate (YMDB00832)

Identification
YMDB IDYMDB00832
Nameall-trans-nonaprenyl diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSolanesyl-PP belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. Based on a literature review very few articles have been published on Solanesyl-PP.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • all-trans-Nonaprenyl diphosphate
  • Diphosphoric acid, mono(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl) ester, (all-E)-
  • Solanesyl diphosphate
  • Solanesyl pyrophosphate
  • Ditrans,hexacis-nonaprenyl diphosphate
  • Ditrans,hexacis-nonaprenyl diphosphoric acid
CAS numberNot Available
WeightAverage: 791.0283
Monoisotopic: 790.50662781
InChI KeyIVLBHBFTRNVIAP-MEGGAXOGSA-N
InChIInChI=1S/C45H76O7P2/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)33-18-34-45(10)35-36-51-54(49,50)52-53(46,47)48/h19,21,23,25,27,29,31,33,35H,11-18,20,22,24,26,28,30,32,34,36H2,1-10H3,(H,49,50)(H2,46,47,48)/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-33+,45-35+
IUPAC Name{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Namesolanesyl-PP
Chemical FormulaC45H76O7P2
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\COP(O)(=O)OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentBactoprenol diphosphates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP8.35ALOGPS
logP13.58ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity239.55 m³·mol⁻¹ChemAxon
Polarizability91.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Terpenoid backbone biosynthesisPW002485 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Terpenoid backbone biosynthesisec00900 Map00900
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5464452900-456fbf10d2eb74542c6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0200027900-e6a36ca80e643e26d0f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3201019100-7f1c604d7d7f547b0fc3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-3434379000-f5c645c1e2ae6d7f7e30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0300000900-fc23106a321bbc9b1aa1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200010000-cc834e0f897c832e68c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9fcecdd44b53bc65fe73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0100003900-b66c25462c6ed24c66cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-0001029300-b8d61358eff908170f99JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016s-0319545300-78e37115e678ffc000cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-a0205c5abdb7052e5eadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1300001900-2f411e26c007f3590a2aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9400000000-c9258da5f7e1bcf30955JSpectraViewer
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
  • Forsgren, M., Attersand, A., Lake, S., Grunler, J., Swiezewska, E., Dallner, G., Climent, I. (2004). "Isolation and functional expression of human COQ2, a gene encoding a polyprenyl transferase involved in the synthesis of CoQ." Biochem J 382:519-526.15153069
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18144
HMDB IDHMDB0002367
Pubchem Compound ID25244603
Kegg IDC04145
ChemSpider ID24808121
FOODB IDFDB112206
Wikipedia IDNot Available
BioCyc IDSOLANESYL-PYROPHOSPHATE

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.