Record Information
Version2.0
Creation Date2012-05-31 14:33:13 -0600
Update Date2015-09-17 16:24:22 -0600
Secondary Accession Numbers
  • ECMDB20208
Identification
Name:Undecaprenyl phosphate
DescriptionUndecaprenyl phosphate 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:
  • C55-PP-GlcNAc-ManNAcA
  • Di-trans,octa-cis-undecaprenyl phosphate
  • Di-trans,octa-cis-undecaprenyl phosphoric acid
  • Lipid II
  • ManNAcA-GlcNAc-PP-lipid
  • ManNAcA-GlcNAc-pyrophosphorylundecaprenol
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate
  • Undecaprenyl dihydrogen phosphate
  • Undecaprenyl dihydrogen phosphoric acid
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphate
  • Undecaprenyl n-acetyl-glucosaminyl-n-acetyl-mannosaminuronic acid pyrophosphoric acid
  • Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphoric acid
  • Undecaprenyl phosphoric acid
  • Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate
  • Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronic acid
  • UnPreP
Chemical Formula:C55H91O4P
Weight:Average: 847.2824
Monoisotopic: 846.665497912
InChI Key:UFPHFKCTOZIAFY-UHFFFAOYSA-N
InChI:InChI=1S/C55H91O4P/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)43-44-59-60(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,(H2,56,57,58)
CAS number:25126-51-6
IUPAC Name:{[(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}phosphonic acid
Traditional IUPAC Name:undecaprenyl phosphate
SMILES:CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as bactoprenol monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a bactoprenyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentBactoprenol monophosphates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol monophosphate
  • Polyprenyl monophosphate
  • 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
Predicted Properties
PropertyValueSource
Water Solubility0.00044 g/LALOGPS
logP9.81ALOGPS
logP17.32ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity276.28 m³·mol⁻¹ChemAxon
Polarizability108.51 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Secondary Metabolites: enterobacterial common antigen biosynthesis 3PW002046 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1111010950-2221cf75248f64bca672View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4231212900-4fe3cb4ad3699e45a24fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-5753333900-3c604a1ec5b3113b92a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-8000000090-90dc5436861ba784ee41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000100-ca3c51a4c99b9c8e852aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-730f754e612aebbf8681View 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
  • 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 ID16141
HMDB IDNot Available
Pubchem Compound ID5280338
Kegg IDC00348
ChemSpider ID4444049
Wikipedia IDBactoprenol
BioCyc IDC55-PP-GLCNAC-MANNACA
EcoCyc IDC55-PP-GLCNAC-MANNACA

Enzymes

General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
First step of the lipid cycle reactions in the biosynthesis of the cell wall peptidoglycan
Gene Name:
mraY
Uniprot ID:
P0A6W3
Molecular weight:
39875
Reactions
UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol.
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 magnesium ion binding
Specific function:
Catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP- C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen. The apparent affinity of WecA for the polyisoprenyl phosphate substrates increases with the polyisoprenyl chain length. WecA is unable to utilize dolichyl phosphate (Dol-P)
Gene Name:
wecA
Uniprot ID:
P0AC78
Molecular weight:
40957
Reactions
UDP-N-acetyl-D-glucosamine + di-trans,octa-cis-undecaprenyl phosphate = UMP + N-acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol.
General function:
Involved in fucosyltransferase activity
Specific function:
Catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA-Fuc4NAc (Lipid III), the third lipid-linked intermediate involved in ECA synthesis
Gene Name:
wecF
Uniprot ID:
P56258
Molecular weight:
40639
Reactions
TDP-Fuc4NAc + Und-PP-GlcNAc-ManNAcA = TDP + Und-PP-GlcNAc-ManNAcA-Fuc4NAc.
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 phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the transfer of 4-deoxy-4-formamido-L- arabinose from UDP to undecaprenyl phosphate. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnC
Uniprot ID:
P77757
Molecular weight:
36339
Reactions
UDP-4-deoxy-4-formamido-beta-L-arabinose + di-trans,octa-cis-undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-alpha-L-arabinose di-trans,octa-cis-undecaprenyl phosphate.
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the transfer of the L-Ara4N moiety of the glycolipid undecaprenyl phosphate-alpha-L-Ara4N to lipid A. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnT
Uniprot ID:
P76473
Molecular weight:
62542
Reactions
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + lipid IV(A) = lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
yeiU
Uniprot ID:
P76445
Molecular weight:
26759
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA (Lipid II), the second lipid-linked intermediate involved in ECA synthesis
Gene Name:
wecG
Uniprot ID:
P27836
Molecular weight:
27928
Reactions
UDP-ManNAcA + Und-PP-GlcNAc = UDP + Und-PP-GlcNAc-ManNAcA.