Record Information
Version2.0
Creation Date2012-05-31 13:53:06 -0600
Update Date2015-06-03 15:54:08 -0600
Secondary Accession Numbers
  • ECMDB01469
Identification
Name:Undecaprenyl diphosphate
DescriptionUndecaprenyl diphosphate belongs to the class of Polyprenyl Phosphates. These are prenol lipids in which the phosphate group is linked to one end of the polyprenol moiety. (inferred from compound structure)C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate) is an essential molecule involved in construction of the bacterial peptidoglycan cell wall. (WikiPedia)
Structure
Thumb
Synonyms:
  • Bactoprenyl pyrophosphate
  • Bactoprenyl pyrophosphoric acid
  • Di-trans,octa-cis-undecaprenyl diphosphate
  • Di-trans-poly-cis-undecaprenyl diphosphate
  • Di-trans,octa-cis-undecaprenyl diphosphate
  • Di-trans,octa-cis-undecaprenyl diphosphoric acid
  • Di-trans-poly-cis-undecaprenyl diphosphate
  • Di-trans-poly-cis-undecaprenyl diphosphoric acid
  • 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) ester
  • Diphosphorate 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) ester
  • 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) ester
  • Undecaprenyl diphosphate
  • Undecaprenyl diphosphoric acid
  • Undecaprenyl pyrophosphate
  • Undecaprenyl pyrophosphate (ambiguous)
  • Undecaprenyl pyrophosphoric acid
  • Undecaprenyl pyrophosphoric acid (ambiguous)
  • Undecaprenyl-PP
  • Undecaprenyl-PP (ambiguous)
  • UndPP
  • UPP
  • UPP (ambiguous)
Chemical Formula:C55H92O7P2
Weight:Average: 927.2623
Monoisotopic: 926.631828322
InChI Key:NTXGVHCCXVHYCL-RDQGWRCRSA-N
InChI: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+
CAS number:23-13-2
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 IUPAC Name:undecaprenyl pyrophosphate
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
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
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:7.736PhysProp
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
Polarizability114.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > Hydrogen ion + Undecaprenyl diphosphate + three linked disacharide pentapeptide murein units (uncrosslinked, middle of chain)
2 Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine >2 Hydrogen ion +2 Undecaprenyl diphosphate + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain)
Water + Undecaprenyl diphosphate > Hydrogen ion + Phosphate + Undecaprenyl phosphate
(O16 antigen)x2 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x3 undecaprenyl diphosphate + Undecaprenyl diphosphate
(O16 antigen)x3 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 undecaprenyl diphosphate + Undecaprenyl diphosphate
2 O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x2 undecaprenyl diphosphate + Undecaprenyl diphosphate
(enterobacterial common antigen)x2 undecaprenyl-diphosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x3 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate
(enterobacterial common antigen)x3 undecaprenyl-diphosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x4 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate
2 Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x2 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate
core oligosaccharide lipid A + Undecaprenyl diphosphate > core oligosaccharide lipid A diphosphate + Undecaprenyl phosphate
core oligosaccharide lipid A + (enterobacterial common antigen)x4 undecaprenyl-diphosphate > (enterobacterial common antigen)x4 core oligosaccharide lipid A + Hydrogen ion + Undecaprenyl diphosphate
core oligosaccharide lipid A + (O16 antigen)x4 undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 core oligosaccharide lipid A + Undecaprenyl diphosphate
di-trans,poly-cis-Undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate
Hydrogen ion + Lipid A-core + Undecaprenyl diphosphate lipid A-core 1-diphosphate + Di-trans,poly-cis-undecaprenyl phosphate
a peptidoglycan + <i>N</i>-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-<i>N</i>-acetylglucosamine > Undecaprenyl diphosphate + a peptidoglycan
a peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Water > a peptidoglycan with D,D cross-links (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate + D-Alanine
Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + Pyrophosphate
N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine > Hydrogen ion + a peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate
Undecaprenyl diphosphate + Water > Hydrogen ion + Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + Undecaprenyl diphosphate
Undecaprenyl diphosphate + Water > di-trans,octa-cis-undecaprenyl phosphate + Inorganic phosphate
[GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine <> Undecaprenyl diphosphate
2 lipid II(A) > Undecaprenyl diphosphate + Hydrogen ion + a peptidoglycan dimer (meso-diaminopimelate containing)

SMPDB Pathways:
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
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
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Ogura K, Koyama T, Sagami H: Polyprenyl diphosphate synthases. Subcell Biochem. 1997;28:57-87. Pubmed: 9090291
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17047
HMDB IDHMDB01469
Pubchem Compound ID5280604
Kegg IDC04574
ChemSpider ID1089
WikipediaUPP
BioCyc IDUNDECAPRENYL-DIPHOSPHATE
EcoCyc IDUNDECAPRENYL-DIPHOSPHATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular weight:
93636
General function:
Involved in catalytic activity
Specific function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular weight:
94292
Reactions
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate.
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:
pgpB
Uniprot ID:
P0A924
Molecular weight:
29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
General function:
Involved in penicillin binding
Specific function:
Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular weight:
63877
Reactions
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate.
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Adds the O-antigen on the glucose group of LPS
Gene Name:
rfaL
Uniprot ID:
P27243
Molecular weight:
46877
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
May link the O-antigen tetrasaccharide units into long chains, giving rise to typical smooth LPS
Gene Name:
rfc
Uniprot ID:
P37748
Molecular weight:
44744
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Generates undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide
Gene Name:
uppS
Uniprot ID:
P60472
Molecular weight:
28444
Reactions
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + di-trans,octa-cis-undecaprenyl diphosphate.
General function:
Involved in undecaprenyl-diphosphatase activity
Specific function:
Catalyzes the dephosphorylation of undecaprenyl diphosphate (UPP). Confers resistance to bacitracin
Gene Name:
uppP
Uniprot ID:
P60932
Molecular weight:
29758
Reactions
Undecaprenyl diphosphate + H(2)O = undecaprenyl phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Overexpression leads to increased undecaprenyl diphosphatase activity and to increased resistance to bacitracin. May have a preferred substrate other than undecaprenyl diphosphate in vivo
Gene Name:
ybjG
Uniprot ID:
P75806
Molecular weight:
22398
Reactions
Undecaprenyl diphosphate + H(2)O = undecaprenyl phosphate + phosphate.
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Confers a modal distribution of chain length on the O- antigen component of lipopolysaccharide (LPS). Gives rise to a reduced number of short chain molecules and increases in numbers of longer molecules
Gene Name:
wzzB
Uniprot ID:
P76372
Molecular weight:
36455
General function:
Involved in catalytic activity
Specific function:
Cell wall formation. The enzyme has a penicillin- insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a transpeptidase C-terminal domain which may not be functional
Gene Name:
pbpC
Uniprot ID:
P76577
Molecular weight:
85066
General function:
Involved in lipid transporter activity
Specific function:
Specific function unknown
Gene Name:
mviN
Uniprot ID:
P0AF16
Molecular weight:
55267
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Specific function unknown
Gene Name:
wzzE
Uniprot ID:
P0AG00
Molecular weight:
39489
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
yeiU
Uniprot ID:
P76445
Molecular weight:
26759
General function:
Not Available
Specific function:
Could be involved in ECA polysaccharide chain elongation
Gene Name:
wzyE
Uniprot ID:
P27835
Molecular weight:
51517

Transporters

General function:
Involved in lipid transporter activity
Specific function:
Specific function unknown
Gene Name:
mviN
Uniprot ID:
P0AF16
Molecular weight:
55267