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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:23 UTC
HMDB IDHMDB0001469
Secondary Accession Numbers
  • HMDB01469
Metabolite Identification
Common NameUndecaprenyl diphosphate
DescriptionIt is noteworthy that in spite of the similarity of the reactions catalyzed by these prenyltransferases, the modes of expression of catalytic function are surprisingly different, varying according to the chain length and stereochemistry of reaction products. These enzymes are summarized and classified into four groups, as shown in Figure 13. Short-chain prenyl diphosphates synthases such as FPP and GGPP synthases require no cofactor except divalent metal ions, Mg2+ or Mn2+, which are commonly required by all prenyl diphosphate synthases. Medium-chain prenyl diphosphate synthases, including the enzymes for the synthesis of all-E-HexPP and all-E-HepPP, are unusual because they each consist of two dissociable dissimilar protein components, neither of which has catalytic activity. The enzymes for the synthesis of long-chain all-E-prenyl diphosphates, including octaprenyl (C40), nonaprenyl-(C45), and decaprenyl (C50) diphosphates, require polyprenyl carrier proteins that remove polyprenyl products from the active sites of the enzymes to maintain efficient turnovers of catalysis. The enzymes responsible for Z-chain elongation include Z,E-nonaprenyl-(C45) and Z,E-undecaprenyl (C55) diphosphate synthases, which require a phospholipid. The classification of mammalian synthases seems to be fundamentally similar to that of bacterial synthases except that no medium-chain prenyl diphosphate synthases are included. The Z-prenyl diphosphate synthase in mammalian cells is dehydrodolichyl PP synthase, which catalyzes much longer chain elongations than do bacterial enzymes. Dehydrodolichyl PP synthase will be a major target of future studies in this field in view of its involvement in glycoprotein biosynthesis. PMID: 9090291 .
Structure
Data?1582752203
Synonyms
ValueSource
Diphosphoric acid, mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) esterChEBI
Undecaprenyl pyrophosphateChEBI
UndPPChEBI
Diphosphate, mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) esterGenerator
Undecaprenyl pyrophosphoric acidGenerator
Undecaprenyl diphosphoric acidGenerator
Bactoprenyl pyrophosphateHMDB
Diphosphoric acid mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) esterHMDB
Undecaprenyl-PPHMDB
UPPHMDB
Chemical FormulaC55H92O7P2
Average Molecular Weight927.2623
Monoisotopic Molecular Weight926.631828322
IUPAC Name{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Nameundecaprenyl pyrophosphate
CAS Registry Number23-13-2
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\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/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+
InChI KeyNTXGVHCCXVHYCL-RDQGWRCRSA-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
  • Polyterpenoid
  • Bactoprenol diphosphate
  • 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

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
logP10(9.29) g/LALOGPS
logP10(16.89) g/LChemAxon
logS10(-6.4) g/LALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity287.15 m³·mol⁻¹ChemAxon
Polarizability114.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+31661259
DarkChem[M-H]-31661259
AllCCS[M+H]+294.19432859911
AllCCS[M-H]-244.06832859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 10V, Positive-QTOFsplash10-0002-0100000954-8fbcdf9ba65fb4f798a42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 20V, Positive-QTOFsplash10-0002-1000000910-edce154fa23a4d389b0f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 40V, Positive-QTOFsplash10-0002-0011021910-1849ab2f92b33143879c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 10V, Negative-QTOFsplash10-004i-0400000009-a76202c14854f25f37012015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 20V, Negative-QTOFsplash10-004i-9400000001-55e96da13b4d53a1bb172015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-04849c4e73cca6e0f4052015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 10V, Negative-QTOFsplash10-004i-0000000009-1645404a3665e531266c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 20V, Negative-QTOFsplash10-004i-2300010029-2f3b24b17d959569ec172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 40V, Negative-QTOFsplash10-056r-9400000000-82cd8a9cc8986cab62602021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 10V, Positive-QTOFsplash10-004i-1100000459-f0ed52e6afe5c429d4752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 20V, Positive-QTOFsplash10-052b-0001001690-18b947d234bc42e4513a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecaprenyl diphosphate 40V, Positive-QTOFsplash10-0gea-0119566130-b9b2aff1eccdac5899232021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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 IDFDB022641
KNApSAcK IDNot Available
Chemspider ID4444213
KEGG Compound IDC03543
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkC55-isoprenyl pyrophosphate
METLIN ID3706
PubChem Compound5280604
PDB IDNot Available
ChEBI ID17047
Food Biomarker OntologyNot Available
VMH IDUDCPDP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ogura K, Koyama T, Sagami H: Polyprenyl diphosphate synthases. Subcell Biochem. 1997;28:57-87. [PubMed:9090291 ]

Enzymes

General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Catalyzes cis-prenyl chain elongation to produce the polyprenyl backbone of dolichol, a glycosyl carrier-lipid required for the biosynthesis of several classes of glycoprotein.
Gene Name:
DHDDS
Uniprot ID:
Q86SQ9
Molecular weight:
Not Available
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Acts as a specific receptor for the N-terminus of Nogo- B, a neural and cardiovascular regulator. Able to regulate vascular remodeling and angiogenesis. Its similarity with UPP synthase proteins suggests that it may act as a scaffold for the binding of isoprenyl lipids and/or prenylated proteins
Gene Name:
NUS1
Uniprot ID:
Q96E22
Molecular weight:
33224.0
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Not Available
Gene Name:
DHDDS
Uniprot ID:
Q5T0A0
Molecular weight:
8307.7
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Not Available
Gene Name:
DHDDS
Uniprot ID:
Q5T0A1
Molecular weight:
24122.0
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Not Available
Gene Name:
DHDDS
Uniprot ID:
Q5T0A2
Molecular weight:
25706.5
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Not Available
Gene Name:
DHDDS
Uniprot ID:
Q5T0A3
Molecular weight:
25205.8
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Not Available
Gene Name:
DHDDS
Uniprot ID:
Q5T0A6
Molecular weight:
19615.2