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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:42 UTC
Update Date2017-10-23 19:06:01 UTC
HMDB IDHMDB0012188
Secondary Accession Numbers
  • HMDB12188
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 KeyNGFSMHKFTZROKJ-MMSZMYIBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentBactoprenol diphosphates
Alternative Parents
Substituents
  • Bactoprenol diphosphate
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • Sesterterpenoid
  • 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 Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 Solubility0.00072 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity168.14 m³·mol⁻¹ChemAxon
Polarizability67.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00tb-7466390000-1a091a15f69aa600fd33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0202690000-ca7be5f91d120b34e02fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2312910000-a18bd263c2252df7e12bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-4439820000-433602f028fdf8312339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0400090000-eba550c0908e0bdcc04fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-7900010000-903a330facd80aef97a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5db7557b14be93fbdd9bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Ubiquinone BiosynthesisPw000039Pw000039 greyscalePw000039 simpleMap00130
Displaying 1 entry
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
METLIN IDNot Available
PubChem Compound5280413
PDB IDNot Available
ChEBI ID17528
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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