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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:45 UTC
HMDB IDHMDB01469
Secondary Accession NumbersNone
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
Thumb
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 diphosphateChEBI
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
all-trans-Undecaprenyl diphosphoric acidGenerator
Undecaprenyl diphosphoric acidGenerator
Undecaprenyl pyrophosphoric 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 KeyInChIKey=NTXGVHCCXVHYCL-RDQGWRCRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000367 mg/mLALOGPS
logP9.29ALOGPS
logP16.89ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count35ChemAxon
Refractivity287.15 m3·mol-1ChemAxon
Polarizability114.77 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0100000954-8fbcdf9ba65fb4f798a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1000000910-edce154fa23a4d389b0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0011021910-1849ab2f92b33143879cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400000009-a76202c14854f25f3701View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000001-55e96da13b4d53a1bb17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-04849c4e73cca6e0f405View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022641
KNApSAcK IDNot Available
Chemspider ID4444213
KEGG Compound IDC03543
BioCyc IDUNDECAPRENYL-DIPHOSPHATE
BiGG IDNot Available
Wikipedia LinkUPP
NuGOwiki LinkHMDB01469
Metagene LinkHMDB01469
METLIN ID3706
PubChem Compound5280604
PDB IDNot Available
ChEBI ID17047
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. [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