Record Information
Version2.0
Creation Date2012-05-31 14:38:34 -0600
Update Date2015-06-03 17:19:45 -0600
Secondary Accession Numbers
  • ECMDB20310
Identification
Name:Di-trans,poly-cis-undecaprenyl phosphate
DescriptionDi-trans,poly-cis-undecaprenyl phosphate is an undecaprenyl phosphate having two (E)- and eight (Z)-double bonds. It is invovled in Peptidoglycan biosynthesis. (KEGG). Escherichia coli and other Gram-negative bacteria utilize the methylerythritol phosphate pathway to synthesize isopentenyl diphosphate and dimethylallyl diphosphate which are the precursors of (2E,6E)-farnesyl diphosphate. The latter compound is a precursor of di-trans,poly-cis-undecaprenyl phosphate, which leads to the biosynthesis of cell wall polymers. Initially (2E,6E)-farnesyl diphosphate is formed by the joining of geranyl diphosphate and isopentenyl diphosphate in a reaction catalyzed by geranyl diphosphate synthase / farnesyl diphosphate synthase encoded by gene ispA. Subsequently multiple units of isopentenyl diphosphate are polymerized to form di-trans,octa-cis-undecaprenyl diphosphate in a series of sequential condensation reactions catalyzed by undecaprenyl diphosphate synthase encoded by gene ispU.
Structure
Thumb
Synonyms:
  • ditrans,octacis-undecaprenyl phosphate
  • ditrans,polycis-undecaprenyl phosphate
  • Di-trans,poly-cis-undecaprenyl phosphoric acid
  • Ditrans,octacis-undecaprenyl phosphate
  • Ditrans,octacis-undecaprenyl phosphoric acid
  • Ditrans,polycis-undecaprenyl phosphate
  • Ditrans,polycis-undecaprenyl phosphoric acid
Chemical Formula:C55H89O4P
Weight:Average: 845.2665
Monoisotopic: 844.649847848
InChI Key:DCZTULDWWVSYKM-UHFFFAOYSA-N
InChI:InChI=1S/C55H89O4P/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/q-1
CAS number:Not Available
IUPAC Name:{dioxo[(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]-λ⁵-phosphanuidyl}oxidanyl
Traditional IUPAC Name:{dioxo[(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]-λ⁵-phosphanuidyl}oxidanyl
SMILES:CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO[P-]([O])(=O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyterpenoids
Direct ParentPolyterpenoids
Alternative Parents
Substituents
  • Polyterpenoid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP9.49ALOGPS
logP15.14ChemAxon
logS-6.6ALOGPS
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity274.04 m³·mol⁻¹ChemAxon
Polarizability108.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
di-trans,poly-cis-Undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate <> Undecaprenyl phosphate alpha-L-Ara4FN + Uridine 5'-diphosphate + 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate
Uridine diphosphate-N-acetylglucosamine + Di-trans,poly-cis-undecaprenyl phosphate <> N-Acetyl-D-glucosaminyldiphosphoundecaprenol + Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol
Undecaprenyl phosphate alpha-L-Ara4N + 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> Lipid IIA + Di-trans,poly-cis-undecaprenyl phosphate
Undecaprenyl phosphate alpha-L-Ara4N + Di[3-deoxy-D-manno-octulosonyl]-lipid IV(A) <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid IVA + Di-trans,poly-cis-undecaprenyl phosphate
Hydrogen ion + Lipid A-core + Undecaprenyl diphosphate lipid A-core 1-diphosphate + Di-trans,poly-cis-undecaprenyl phosphate
Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine 5'-monophosphate
KDO2-Lipid A + 4-amino-4-deoxy-&alpha;-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate > L-Ara4N-modified KDO2-Lipid A + Di-trans,poly-cis-undecaprenyl phosphate
Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate > 4-deoxy-4-formamido-&alpha;-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate + Uridine 5'-diphosphate
Undecaprenyl diphosphate + Water > Hydrogen ion + Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA
UDP-Glucose + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + alpha-D-Glucopyranosyl-diphospho-ditrans,octacis-undecaprenol
di-trans,octa-cis-undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate
undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA
SMPDB Pathways:Not Available
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Cationic antimicrobial peptide (CAMP) resistance eco01503
  • Metabolic pathways eco01100
  • Peptidoglycan biosynthesis ec00550
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25202932
Kegg IDC17556
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-9646
EcoCyc IDCPD-9646

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 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