You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-04-06 16:20:42 UTC
Update Date2016-02-11 01:23:48 UTC
HMDB IDHMDB12188
Secondary Accession NumbersNone
Metabolite Identification
Common NameAll-trans-hexaprenyl diphosphate
DescriptionAll-trans-hexaprenyl diphosphate is the final product of hexaprenyl diphosphate biosynthesis pathway.In this pathway multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form various polyisoprenoids. There are two different pathways for the biosynthesis of IPP. Bacteria that possess ubiquinone generally use the methylerythritol phosphate pathway (MEP), while the eukaryotic microorganisms use the mevalonate pathway. However, exceptions exist - for example, some eukaryotic microbes, like the green algae and the malarial parasite Plasmodium falciparum , appear to utilize the MEP pathway, and some bacteria utilze the mevalonate pathway [ Eisenreich01 , Eisenreich04 ]. In Saccharomyces cerevisiae S288C the initial addition of two isoprenyl units to form (E,E)-farnesyl diphosphate is catalyzed by geranyltransferase / dimethylallyltransferase , encoded by FPP1. An additional unit is added by farnesyltranstransferase (encoded by BTS1 ), resulting in formation of all-trans-geranyl-geranyl diphosphate. The last enzyme in this pathway is hexaprenyl diphosphate synthase (encoded by COQ1 ), which adds additional isoprenoid units to a maximal length unique to the organism. In the case of Saccharomyces cerevisiae S288C , it is 6 units. Polyprenyl diphosphate synthase enzymes, such as hexaprenyl diphosphate synthase , are responsible for determining the final length of the tail. When yeast COQ1 mutants are complemented with homologs from other organisms, ubiquinone biosynthesis is restored, but the tail lenghth of the quinone depends on the source of the enzyme.
Structure
Thumb
Synonyms
ValueSource
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphateChEBI
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphoric acidGenerator
all-trans-Hexaprenyl diphosphoric acidGenerator
(e)-Hexaprenyl diphosphateHMDB
Chemical FormulaC30H52O7P2
Average Molecular Weight586.6772
Monoisotopic Molecular Weight586.318827042
IUPAC Name[({[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\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
InChI Identifier
InChI=1S/C30H52O7P2/c1-25(2)13-8-14-26(3)15-9-16-27(4)17-10-18-28(5)19-11-20-29(6)21-12-22-30(7)23-24-36-39(34,35)37-38(31,32)33/h13,15,17,19,21,23H,8-12,14,16,18,20,22,24H2,1-7H3,(H,34,35)(H2,31,32,33)/b26-15+,27-17+,28-19+,29-21+,30-23+
InChI KeyInChIKey=NGFSMHKFTZROKJ-MMSZMYIBSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Bactoprenol diphosphate
  • Sesterterpenoid
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000715 mg/mLALOGPS
logP5.95ALOGPS
logP8.6ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity168.14 m3·mol-1ChemAxon
Polarizability67.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Ubiquinone BiosynthesisSMP00065map00130
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028840
KNApSAcK IDNot Available
Chemspider ID4444089
KEGG Compound IDC01230
BioCyc IDALL-TRANS-HEXAPRENYL-DIPHOSPHATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12188
Metagene LinkHMDB12188
METLIN IDNot Available
PubChem Compound5280413
PDB IDNot Available
ChEBI ID17528
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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:
Q96H96
Molecular weight:
45593.67
Reactions
All-trans-hexaprenyl diphosphate + 4-Hydroxybenzoic acid → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphatedetails