Showing metabocard for Presqualene diphosphate (BMDB0001278)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:32 UTC
Update Date2020-04-22 15:07:27 UTC
BMDB IDBMDB0001278
Secondary Accession Numbers
  • BMDB01278
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
MOLSDFPDBSMILESInChI
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@@]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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability66.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001278
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
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

Enzyme Details
1. Squalene synthase
General function:
Lipid transport and metabolism
Specific function:
Critical branch point enzyme of isoprenoid biosynthesis that is thought to regulate the flux of isoprene intermediates through the sterol pathway.
Gene Name:
FDFT1
Uniprot ID:
Q32KR6
Molecular weight:
48304.0