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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
Data?1594314828
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
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
Polarizability66.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+239.95231661259
DarkChem[M-H]-223.18131661259
AllCCS[M+H]+242.73732859911
AllCCS[M-H]-241.86632859911
DeepCCS[M+H]+228.27630932474
DeepCCS[M-H]-226.45130932474
DeepCCS[M-2H]-259.69330932474
DeepCCS[M+Na]+233.88230932474
AllCCS[M+H]+242.732859911
AllCCS[M+H-H2O]+241.332859911
AllCCS[M+NH4]+244.032859911
AllCCS[M+Na]+244.432859911
AllCCS[M-H]-241.932859911
AllCCS[M+Na-2H]-245.832859911
AllCCS[M+HCOO]-250.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Presqualene diphosphateCC(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)C4408.9Standard polar33892256
Presqualene diphosphateCC(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)C3349.5Standard non polar33892256
Presqualene diphosphateCC(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)C3849.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Presqualene diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3756.0Semi standard non polar33892256
Presqualene diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3230.6Standard non polar33892256
Presqualene diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4796.1Standard polar33892256
Presqualene diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3750.5Semi standard non polar33892256
Presqualene diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3242.7Standard non polar33892256
Presqualene diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4835.0Standard polar33892256
Presqualene diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3725.4Semi standard non polar33892256
Presqualene diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3288.0Standard non polar33892256
Presqualene diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4336.3Standard polar33892256
Presqualene diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3721.2Semi standard non polar33892256
Presqualene diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3280.2Standard non polar33892256
Presqualene diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4339.1Standard polar33892256
Presqualene diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3693.9Semi standard non polar33892256
Presqualene diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3321.1Standard non polar33892256
Presqualene diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3845.1Standard polar33892256
Presqualene diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3943.1Semi standard non polar33892256
Presqualene diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3383.6Standard non polar33892256
Presqualene diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4856.6Standard polar33892256
Presqualene diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3933.5Semi standard non polar33892256
Presqualene diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3402.6Standard non polar33892256
Presqualene diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4891.0Standard polar33892256
Presqualene diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4077.1Semi standard non polar33892256
Presqualene diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3581.4Standard non polar33892256
Presqualene diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4408.1Standard polar33892256
Presqualene diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4069.6Semi standard non polar33892256
Presqualene diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C3562.9Standard non polar33892256
Presqualene diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/[C@H]1[C@H](COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@]1(C)CC/C=C(\C)CCC=C(C)C4435.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Presqualene diphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gia-4200490000-9a3a83875f6f2ef2cddb2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 10V, Positive-QTOFsplash10-0a4r-0200690000-b880904a199b28acdc232016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 20V, Positive-QTOFsplash10-0a4i-2352900000-82d62bcceb1656998b102016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 40V, Positive-QTOFsplash10-0a6r-3366920000-574a4a9be60ca4c8d7652016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 10V, Negative-QTOFsplash10-000i-0500090000-557817e75ec0eed286722016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 20V, Negative-QTOFsplash10-056r-9800020000-6bca51e71e8dd45015232016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-0fe8c0f845a21c70b30c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 10V, Negative-QTOFsplash10-000i-0100090000-5247a3c4a85015b072da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 20V, Negative-QTOFsplash10-002r-2200090000-09d9e50734c089804e412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 40V, Negative-QTOFsplash10-004i-9100000000-7dab7bce5c804b18ac2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 10V, Positive-QTOFsplash10-000i-0232590000-730292814c7f9261de9b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 20V, Positive-QTOFsplash10-014j-3402890000-7a23c1768de1e2a2244f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Presqualene diphosphate 40V, Positive-QTOFsplash10-014i-9317500000-d5d421cf8356319353442021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
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