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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:09 UTC
HMDB IDHMDB0001278
Secondary Accession Numbers
  • HMDB01278
Metabolite Identification
Common NamePresqualene diphosphate
DescriptionPresqualene diphosphate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Presqualene diphosphate is a moderately acidic compound (based on its pKa).
Structure
Thumb
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
Presqualene diphosphateHMDB
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@H]1[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
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
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 IDFDB022531
KNApSAcK IDNot Available
Chemspider ID4444207
KEGG Compound IDC03428
BioCyc IDCPD-465
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6132
PubChem Compound5280592
PDB IDNot Available
ChEBI ID15442
Food Biomarker OntologyNot Available
VMH IDHC01118
MarkerDB IDNot Available
Good Scents 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