all-trans-octaprenyl diphosphate (PAMDB110808)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110808
Identification
Name: all-trans-octaprenyl diphosphate
Description:Trianion of all-trans-octaprenyl diphosphate arising from deprotonation of all three diphosphate OH groups; major species at pH 7.3
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • farnesylfarnesylgeranyl-PP
  • octaprenyl pyrophosphate
  • OPP
  • farnesylfarnesylgeraniol
  • octaprenyl diphosphate
Chemical Formula: C40H65O7P2
Average Molecular Weight: 719.9
Monoisotopic Molecular Weight: 722.4440275575
InChI Key: IKKLDISSULFFQO-DJMILUHSSA-K
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)/p-3/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+
CAS number: Not Available
IUPAC Name:(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 diphosphate
Traditional IUPAC Name: octaprenyl pyrophosphate
SMILES:CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassPrenol lipids
Direct Parent Tetraterpenoids
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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00037 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity215.74 m3·mol-1ChemAxon
Polarizability86.26 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate → all-trans-octaprenyl diphosphate + diphosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
References
References:
  • 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. [8765142 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI57711
HMDBHMDB01094
IAF126043243
KEGGC04146
PubChem25245331