Record Information
Version2.0
Creation Date2012-05-31 13:45:03 -0600
Update Date2015-06-03 15:53:43 -0600
Secondary Accession Numbers
  • ECMDB01094
Identification
Name:Octaprenyl diphosphate
DescriptionOctaprenyl diphosphate belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)Octaprenyl diphosphate is invovled in Terpenoid backbone biosynthesis, Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)
Structure
Thumb
Synonyms:
  • All-trans-octaprenyl diphosphate
  • all-trans-Octaprenyl diphosphoric acid
  • Farnesylfarnesylgeraniol
  • Octaprenyl diphosphate
  • Octaprenyl diphosphoric acid
  • Octaprenyl pyrophosphate
  • Octaprenyl pyrophosphoric acid
  • Octaprenyl-PP
  • OPP
  • OPrPP
Chemical Formula:C40H68O7P2
Weight:Average: 722.9112
Monoisotopic: 722.444027554
InChI Key:IKKLDISSULFFQO-DJMILUHSSA-N
InChI:InChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+
CAS number:Not Available
IUPAC Name:{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name:octaprenyl pyrophosphate
SMILES:CC(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\COP(O)(=O)OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentTetraterpenoids
Alternative Parents
Substituents
  • Tetraterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Isoprenoid phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:5.072PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
logP7.6ALOGPS
logP11.92ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity215.74 m³·mol⁻¹ChemAxon
Polarizability86.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Menaquinol biosythesisPW001897 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesis 2PW002036 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesisPW000958 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Terpenoid backbone biosynthesis ec00900
  • Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar4-9586675700-c09c2172d7687ee2bec8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0595-0201096600-12d9480675cd5f367894View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3212193000-99403f42aaf79fd7add2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ke-2335391000-ecd9b80ad726186992c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0400000900-88615cb1e1738fc988daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-62cd480f8009a6a20390View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fdd80c5aec3a18d6c4d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-0e05243384d31408f117View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2400012900-2af9ecf51e941f2cf27eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9400000000-12bf027442e46427ee3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1100045900-3d26e24195e3426533cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7n-0001189000-532965cd65681f27a370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02dj-0529441000-76d7ae0a97092fd5d7a8View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Okada K, Suzuki K, Kamiya Y, Zhu X, Fujisaki S, Nishimura Y, Nishino T, Nakagawa T, Kawamukai M, Matsuda H: Polyprenyl diphosphate synthase essentially defines the length of the side chain of ubiquinone. Biochim Biophys Acta. 1996 Aug 16;1302(3):217-23. Pubmed: 8765142
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16275
HMDB IDHMDB01094
Pubchem Compound ID5280651
Kegg IDC04146
ChemSpider ID4444251
Wikipedia IDNot Available
BioCyc IDCPD-9454
EcoCyc IDCPD-9454
Ligand ExpoOTP

Enzymes

General function:
Involved in transferase activity
Specific function:
Conversion of 1,4-dihydroxy-2-naphthoate (DHNA) to dimethylmenaquinone (DMK). Attaches octaprenylpyrophosphate, a membrane-bound 40-carbon side chain to DHNA. The conversion of DHNA to DMK proceeds in three stages:the removal of the carboxyl group of DHNA as CO(2), the attachment of the isoprenoid side chain, and a quinol-to-quinone oxidation, which is thought to be spontaneous
Gene Name:
menA
Uniprot ID:
P32166
Molecular weight:
33594
Reactions
An all-trans-polyprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO(2).
General function:
Involved in prenyltransferase activity
Specific function:
Synthesis of 3-octaprenyl-4-hydroxybenzoate
Gene Name:
ubiA
Uniprot ID:
P0AGK1
Molecular weight:
32511
Reactions
4-hydroxybenzoate + farnesylfarnesylgeraniol = 3-octaprenyl-4-hydroxybenzoate.
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Supplies octaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone
Gene Name:
ispB
Uniprot ID:
P0AD57
Molecular weight:
35217
Reactions
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate.