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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-16 22:31:53 UTC
Update Date2022-03-07 02:51:03 UTC
HMDB IDHMDB0011116
Secondary Accession Numbers
  • HMDB11116
Metabolite Identification
Common NamePhytyl diphosphate
DescriptionPhytyl diphosphate belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Based on a literature review a small amount of articles have been published on Phytyl diphosphate.
Structure
Data?1582752869
Synonyms
ValueSource
Phytyl diphosphoric acidGenerator
Chemical FormulaC20H42O7P2
Average Molecular Weight456.4908
Monoisotopic Molecular Weight456.240576722
IUPAC Name{[hydroxy({[(2E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Namephytyl diphosphate
CAS Registry NumberNot Available
SMILES
CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C20H42O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h15,17-19H,6-14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b20-15+
InChI KeyITPLBNCCPZSWEU-HMMYKYKNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP4.8ALOGPS
logP6.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity117.98 m³·mol⁻¹ChemAxon
Polarizability49.43 ųChemAxon
Number of Rings0ChemAxon
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]+209.36631661259
DarkChem[M-H]-202.97631661259
DeepCCS[M+H]+196.3730932474
DeepCCS[M-H]-192.62230932474
DeepCCS[M-2H]-228.89230932474
DeepCCS[M+Na]+205.18530932474
AllCCS[M+H]+218.132859911
AllCCS[M+H-H2O]+216.232859911
AllCCS[M+NH4]+219.832859911
AllCCS[M+Na]+220.332859911
AllCCS[M-H]-208.532859911
AllCCS[M+Na-2H]-211.432859911
AllCCS[M+HCOO]-214.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phytyl diphosphateCC(C)CCCC(C)CCCC(C)CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O3780.2Standard polar33892256
Phytyl diphosphateCC(C)CCCC(C)CCCC(C)CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O2703.8Standard non polar33892256
Phytyl diphosphateCC(C)CCCC(C)CCCC(C)CCC\C(C)=C\COP(O)(=O)OP(O)(O)=O3105.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phytyl diphosphate,1TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CCCC(C)CCCC(C)CCCC(C)C3093.5Semi standard non polar33892256
Phytyl diphosphate,1TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CCCC(C)CCCC(C)CCCC(C)C2684.5Standard non polar33892256
Phytyl diphosphate,1TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CCCC(C)CCCC(C)CCCC(C)C3904.7Standard polar33892256
Phytyl diphosphate,1TMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3062.2Semi standard non polar33892256
Phytyl diphosphate,1TMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C2693.2Standard non polar33892256
Phytyl diphosphate,1TMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3944.3Standard polar33892256
Phytyl diphosphate,2TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3057.4Semi standard non polar33892256
Phytyl diphosphate,2TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C2794.1Standard non polar33892256
Phytyl diphosphate,2TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3546.8Standard polar33892256
Phytyl diphosphate,2TMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3076.1Semi standard non polar33892256
Phytyl diphosphate,2TMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C2780.6Standard non polar33892256
Phytyl diphosphate,2TMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3536.0Standard polar33892256
Phytyl diphosphate,3TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3097.4Semi standard non polar33892256
Phytyl diphosphate,3TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C2895.8Standard non polar33892256
Phytyl diphosphate,3TMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3171.2Standard polar33892256
Phytyl diphosphate,1TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)CCCC(C)CCCC(C)CCCC(C)C3299.2Semi standard non polar33892256
Phytyl diphosphate,1TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)CCCC(C)CCCC(C)CCCC(C)C2848.3Standard non polar33892256
Phytyl diphosphate,1TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)CCCC(C)CCCC(C)CCCC(C)C4005.2Standard polar33892256
Phytyl diphosphate,1TBDMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3273.6Semi standard non polar33892256
Phytyl diphosphate,1TBDMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C2860.2Standard non polar33892256
Phytyl diphosphate,1TBDMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C4034.5Standard polar33892256
Phytyl diphosphate,2TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3449.8Semi standard non polar33892256
Phytyl diphosphate,2TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3105.8Standard non polar33892256
Phytyl diphosphate,2TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3669.0Standard polar33892256
Phytyl diphosphate,2TBDMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3462.2Semi standard non polar33892256
Phytyl diphosphate,2TBDMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3081.4Standard non polar33892256
Phytyl diphosphate,2TBDMS,isomer #2C/C(=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3686.4Standard polar33892256
Phytyl diphosphate,3TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3650.5Semi standard non polar33892256
Phytyl diphosphate,3TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3323.7Standard non polar33892256
Phytyl diphosphate,3TBDMS,isomer #1C/C(=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CCCC(C)CCCC(C)CCCC(C)C3388.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phytyl diphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-9836200000-e105389dd8325128f3152017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phytyl diphosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 10V, Positive-QTOFsplash10-056r-1293600000-520630b96fd5d36e401b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 20V, Positive-QTOFsplash10-004i-4391000000-0fc147e6567238df452a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 40V, Positive-QTOFsplash10-0kdi-6490000000-b4f44ac407eb006b751b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 10V, Negative-QTOFsplash10-0a4i-0400900000-fdbb63f463b1b1e05e8b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 20V, Negative-QTOFsplash10-004i-9210000000-3cf45ac9b2924695bb452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-9fcecdd44b53bc65fe732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 10V, Positive-QTOFsplash10-0a4i-0001900000-5dcab2f23182eba4625e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 20V, Positive-QTOFsplash10-004i-1296000000-55c24973b98a2dd44c8d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 40V, Positive-QTOFsplash10-0adi-7920000000-54b5f548eaf87e4154672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 10V, Negative-QTOFsplash10-0a4i-0000900000-88bf045f3b9c60ebac1b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 20V, Negative-QTOFsplash10-0a4i-2201900000-ce45eea952643a87e7362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phytyl diphosphate 40V, Negative-QTOFsplash10-056r-9500000000-e41fda1929e93204910c2021-09-22Wishart 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 IDFDB027898
KNApSAcK IDC00007255
Chemspider ID4444345
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280787
PDB IDNot Available
ChEBI ID18187
Food Biomarker OntologyNot Available
VMH IDPHYLDPP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.