Di-trans,poly-cis-undecaprenyl phosphate (PAMDB001145)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001145
Identification
Name: Di-trans,poly-cis-undecaprenyl phosphate
Description:Di-trans,poly-cis-undecaprenyl phosphate is an undecaprenyl phosphate having two (E)- and eight (Z)-double bonds. It is invovled in Peptidoglycan biosynthesis. (KEGG). Pseudomonas aeruginosa 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 845.2665
Monoisotopic Molecular Weight: 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]-???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]-???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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassPolyterpenoids
Direct Parent Polyterpenoids
Alternative Parents
Substituents
  • Polyterpenoid
  • Tetraterpenoid
  • Organic oxide
  • Hydrocarbon derivative
  • Organic anion
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000236 mg/mLALOGPS
logP9.49ALOGPS
logP15.14ChemAxon
logS-6.6ALOGPS
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count33ChemAxon
Refractivity274.04 m3·mol-1ChemAxon
Polarizability108.06 Å3ChemAxon
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
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
Pathways:
Spectra
Spectra:
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

Protein Details
• Phospho-N-acetylmuramoyl-pentapeptide-transferase
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
Locus Tag:
PA4415
Molecular weight:
39.7 kDa
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.
Protein Details
• Undecaprenyl-diphosphatase
General function:
Involved in undecaprenyl-diphosphatase activity
Specific function:
Catalyzes the dephosphorylation of undecaprenyl diphosphate (UPP). Confers resistance to bacitracin
Gene Name:
uppP
Locus Tag:
PA1959
Molecular weight:
30.7 kDa
Reactions
Undecaprenyl diphosphate + H(2)O = undecaprenyl phosphate + phosphate.
Protein Details
• Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase
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
Locus Tag:
PA3553
Molecular weight:
37.3 kDa
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.
Protein Details
• Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase
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
Locus Tag:
PA3556
Molecular weight:
61.7 kDa
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.