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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:51 UTC
HMDB IDHMDB0001278
Secondary Accession Numbers
  • HMDB01278
Metabolite Identification
Common NamePresqualene diphosphate
DescriptionPresqualene diphosphate is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Farnesyl-diphosphate farnesyltransferase.
Structure
Data?1563860691
Synonyms
ValueSource
[(1S,2S,3S)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphateChEBI
[(1S,2S,3S)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphoric acidGenerator
Presqualene diphosphoric acidGenerator
[(1R,2R,3R)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphateHMDB
[(1R,2R,3R)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphoric acidHMDB
(1alpha,2beta(e),3beta(1E,5E))-Diphosphoric acid mono((2-(4,8-dimethyl-3,7-nonadienyl)-2-methyl-3-(2,6,10-trimethyl-1,5,9-undecatrienyl)cyclopropyl)methyl) esterHMDB
Presqualene pyrophosphateHMDB
Chemical FormulaC30H52O7P2
Average Molecular Weight586.6772
Monoisotopic Molecular Weight586.318827042
IUPAC Name[({[(1S,2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Namepresqualene diphosphate
CAS Registry Number29849-75-0
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\[C@@]1([H])[C@]([H])(COP(O)(=O)OP(O)(O)=O)[C@@]1(C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C30H52O7P2/c1-23(2)13-9-15-25(5)17-11-18-27(7)21-28-29(22-36-39(34,35)37-38(31,32)33)30(28,8)20-12-19-26(6)16-10-14-24(3)4/h13-14,17,19,21,28-29H,9-12,15-16,18,20,22H2,1-8H3,(H,34,35)(H2,31,32,33)/b25-17+,26-19+,27-21+/t28-,29-,30-/m0/s1
InChI KeyATZKAUGGNMSCCY-VYCBRMPGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring 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 Solubility0.0011 g/LALOGPS
logP5.31ALOGPS
logP8ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity165.33 m³·mol⁻¹ChemAxon
Polarizability66.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gia-4200490000-9a3a83875f6f2ef2cddbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0200690000-b880904a199b28acdc23JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2352900000-82d62bcceb1656998b10JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3366920000-574a4a9be60ca4c8d765JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0500090000-557817e75ec0eed28672JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9800020000-6bca51e71e8dd4501523JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0fe8c0f845a21c70b30cJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
FoodDB IDFDB022531
KNApSAcK IDNot Available
Chemspider ID4444207
KEGG Compound IDC03428
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6132
PubChem Compound5280592
PDB IDNot Available
ChEBI ID15442
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceRogers, Daniel H.; Yi, Eugene C.; Poulter, C. Dale. Enantioselective Synthesis of (+)-Presqualene Diphosphate. Journal of Organic Chemistry (1995), 60(4), 941-5.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
FDFT1
Uniprot ID:
P37268
Molecular weight:
48114.87
Reactions
Farnesyl pyrophosphate → Pyrophosphate + Presqualene diphosphatedetails
Presqualene diphosphate + NADPH + Hydrogen Ion → Pyrophosphate + Squalene + NADPdetails