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Identification
YMDB IDYMDB00222
Namedi-trans,poly-cis-undecaprenyl diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiondi-trans,octa-cis-undecaprenyl diphosphate, also known as undecaprenyl diphosphate or bactoprenyl diphosphoric acid, 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. di-trans,octa-cis-undecaprenyl diphosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • Bactoprenyl diphosphate
  • di-trans,poly-cis-undecaprenyl diphosphate
  • ditrans,octacis-Undecaprenyl diphosphate
  • ditrans,polycis-undecaprenyl diphosphate
  • Undecaprenyl diphosphate
  • Bactoprenyl diphosphoric acid
  • Di-trans,poly-cis-undecaprenyl diphosphoric acid
  • Undecaprenyl diphosphoric acid
  • Ditrans,octacis-undecaprenyl diphosphoric acid
  • Di-trans,octa-cis-undecaprenyl diphosphoric acid
  • Ditrans,polycis-undecaprenyl diphosphoric acid
CAS number31867-59-1
WeightAverage: 927.2623
Monoisotopic: 926.631828322
InChI KeyNTXGVHCCXVHYCL-NTDVEAECSA-N
InChIInChI=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-
IUPAC Name{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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 IUPAC Name{hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxyphosphoryl}oxyphosphonic acid
Chemical FormulaC55H92O7P2
SMILESCC(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
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
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity287.15 m³·mol⁻¹ChemAxon
Polarizability110.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Terpenoid backbone biosynthesisPW002485 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Terpenoid backbone biosynthesisec00900 Map00900
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0100000954-6107ee97da47f9d14b19JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1000000910-e30642c2c0d28e838b40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0011021910-4da936216a8f0a0c9f2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0400000009-1d1ab3f275e2ed875c74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-7900000001-d21bcc09706c1ed914e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-81ab0f70b7b49058f273JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18197
HMDB IDNot Available
Pubchem Compound ID5280700
Kegg IDC04574
ChemSpider IDNot Available
FOODB IDNot Available
Wikipediadi-trans,poly-cis-undecaprenyl_diphosphate
BioCyc IDNot Available

Enzymes

General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Generates undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP)
Gene Name:
NUS1
Uniprot ID:
Q12063
Molecular weight:
42556.69922
Reactions
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate → 8 diphosphate + di-trans,octa-cis-undecaprenyl diphosphate.