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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001094
Secondary Accession Numbers
  • HMDB01094
Metabolite Identification
Common NameOctaprenyl diphosphate
DescriptionOctaprenyl diphosphate, also known as farnesylfarnesylgeraniol or OPP, belongs to the class of organic compounds known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units. Octaprenyl diphosphate is the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone. It is a substrate of the enzyme trans-octaprenyltranstransferase (EC 2.5.1.11) in the steroid biosynthesis pathway.
Structure
Thumb
Synonyms
ValueSource
(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-OCTAMETHYLDOTRIACONTA-2,6,10,14,18,22,26,30-octaenyl trihydrogen diphosphATEChEBI
all-trans-Octaprenyl pyrophosphateChEBI
FarnesylfarnesylgeraniolChEBI
(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-OCTAMETHYLDOTRIACONTA-2,6,10,14,18,22,26,30-octaenyl trihydrogen diphosphoric acidGenerator
all-trans-Octaprenyl pyrophosphoric acidGenerator
Octaprenyl diphosphoric acidGenerator
all-trans-Octaprenyl diphosphateHMDB
Octaprenyl pyrophosphateHMDB
OPPHMDB
Chemical FormulaC40H68O7P2
Average Molecular Weight722.9112
Monoisotopic Molecular Weight722.444027554
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 Nameoctaprenyl pyrophosphate
CAS Registry Number64732-94-1
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
InChI Identifier
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+
InChI KeyIKKLDISSULFFQO-DJMILUHSSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022423
KNApSAcK IDNot Available
Chemspider ID4444251
KEGG Compound IDC04146
BioCyc IDOCTAPRENYL-DIPHOSPHATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6000
PubChem Compound5280651
PDB IDNot Available
ChEBI ID16275
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]