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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:41 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012187
Secondary Accession Numbers
  • HMDB12187
Metabolite Identification
Common Nameall-trans-Heptaprenyl diphosphate
Descriptionall-trans-Heptaprenyl diphosphate is the final product of the heptaprenyl diphosphate biosynthesis pathway. In this pathway, multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form a polyisoprenoid chain. The sequential addition of isoprenyl units to all-trans-farnesyl diphosphate is performed by polyprenyl diphosphate synthase enzymes such as the E. coli enzyme octaprenyl diphosphate synthase. Additional isoprenoid units are added to a maximal length that is determined by the specific enzyme. Most organisms generate polyprenyl chains of predominantly one length. Once completed, the polyprenyl chain is incorporated into other molecules, such as quinones. The enzyme that attaches the polyprenyl chain to the quinone precursor molecule does not have a preference for any particular length. Thus, the length of the polyprenyl chain in the mature quinone molecule is determined by the predominant polyprenyl diphosphate synthase enzyme of the organism. In most organisms, there is one type of predominant quinone, with a specific polyprenyl chain length. However, most organisms also have minor amounts of quinones with a different polyprenyl chain length. Organisms whose main quinone contains a chain of 7 isoprenyl units include some Gram-negative bacteria (e.g. the gliding bacterium Flexibacter elegans and the phototroph Allochromatium vinosum strain D), but mostly Gram-positive bacteria, such as many members of the Bacillus, Staphylococcus, and Listeria genera.
Structure
Data?1584034749
Synonyms
ValueSource
all-trans-Heptaprenyl diphosphoric acidGenerator
(E)-Heptaprenyl diphosphateHMDB
Chemical FormulaC35H60O7P2
Average Molecular Weight654.7942
Monoisotopic Molecular Weight654.381427298
IUPAC Name[({[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number76078-18-7
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C35H60O7P2/c1-29(2)15-9-16-30(3)17-10-18-31(4)19-11-20-32(5)21-12-22-33(6)23-13-24-34(7)25-14-26-35(8)27-28-41-44(39,40)42-43(36,37)38/h15,17,19,21,23,25,27H,9-14,16,18,20,22,24,26,28H2,1-8H3,(H,39,40)(H2,36,37,38)/b30-17+,31-19+,32-21+,33-23+,34-25+,35-27+
InChI KeyLSJLEXWXRKTZAJ-YUIIPXGZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentBactoprenol diphosphates
Alternative Parents
Substituents
  • Bactoprenol diphosphate
  • Sesquaterpenoid
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • 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
Disposition

Biological location

Source

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 Solubility0.00042 g/LALOGPS
logP6.77ALOGPS
logP10.26ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity191.94 m³·mol⁻¹ChemAxon
Polarizability75.6 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]+253.46931661259
DarkChem[M-H]-239.44631661259
DeepCCS[M+H]+244.90930932474
DeepCCS[M-H]-242.51530932474
DeepCCS[M-2H]-275.39630932474
DeepCCS[M+Na]+250.64930932474
AllCCS[M+H]+259.432859911
AllCCS[M+H-H2O]+258.232859911
AllCCS[M+NH4]+260.532859911
AllCCS[M+Na]+260.832859911
AllCCS[M-H]-248.932859911
AllCCS[M+Na-2H]-253.632859911
AllCCS[M+HCOO]-259.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
all-trans-Heptaprenyl diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O5058.4Standard polar33892256
all-trans-Heptaprenyl diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O3761.6Standard non polar33892256
all-trans-Heptaprenyl diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O4451.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
all-trans-Heptaprenyl diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O4423.9Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O3531.5Standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O5371.5Standard polar33892256
all-trans-Heptaprenyl diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C4431.3Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C3535.6Standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C5398.0Standard polar33892256
all-trans-Heptaprenyl diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C4325.8Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C3578.5Standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C4850.9Standard polar33892256
all-trans-Heptaprenyl diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4320.0Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3555.5Standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4857.0Standard polar33892256
all-trans-Heptaprenyl diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4247.5Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3603.7Standard non polar33892256
all-trans-Heptaprenyl diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4253.5Standard polar33892256
all-trans-Heptaprenyl diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O4609.5Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3667.1Standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O5416.2Standard polar33892256
all-trans-Heptaprenyl diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C4601.3Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3677.3Standard non polar33892256
all-trans-Heptaprenyl diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C5434.9Standard polar33892256
all-trans-Heptaprenyl diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C4716.6Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3853.0Standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C4883.8Standard polar33892256
all-trans-Heptaprenyl diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4716.7Semi standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3823.1Standard non polar33892256
all-trans-Heptaprenyl diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4916.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - all-trans-Heptaprenyl diphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00n1-9576685000-6e83dac11e4fc43aec702017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 10V, Positive-QTOFsplash10-056r-0201957000-65305ee9667b64f15c982016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 20V, Positive-QTOFsplash10-004i-2212920000-e866a47207e7b183f9332016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 40V, Positive-QTOFsplash10-004i-2124920000-4f8f9ed97147bdcff9362016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 10V, Negative-QTOFsplash10-0udi-0400009000-ef57df803e13f978af8b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 20V, Negative-QTOFsplash10-056r-7900001000-dabfe2bedf8d4b023b302016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-b87689e359079a3306be2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 10V, Positive-QTOFsplash10-0a4i-0100059000-7a86c92df6b3b6796d232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 20V, Positive-QTOFsplash10-00pr-0001791000-1ac3025df2725726f9f12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 40V, Positive-QTOFsplash10-01ta-0839611000-29eebde32b7ab4e8c9072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 10V, Negative-QTOFsplash10-0udi-0000009000-93a9138e9fafa8db117b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 20V, Negative-QTOFsplash10-0udi-2400039000-3793d5ead6be5679dad72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - all-trans-Heptaprenyl diphosphate 40V, Negative-QTOFsplash10-056r-9400000000-930b75c463f0d20728232021-09-24Wishart 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 IDFDB028839
KNApSAcK IDNot Available
Chemspider ID4444257
KEGG Compound IDC04216
BioCyc IDALL-TRANS-HEPTAPRENYL-DIPHOSPHATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280658
PDB IDNot Available
ChEBI ID17613
Food Biomarker OntologyNot Available
VMH IDNot Available
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.