P. aeruginosa Metabolome Database: Undecaprenyl phosphate (PAMDB001054)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001054

Identification

Name:

Undecaprenyl phosphate

Description:

Undecaprenyl 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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

847.2824

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Bactoprenol monophosphates

Alternative Parents

Substituents

Polyterpenoid
Tetraterpenoid
Bactoprenol monophosphate
Polyprenyl monophosphate
Isoprenoid phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

undecaprenyl phosphate (CHEBI:16141 )
Bactoprenol monophosphates (C00348 )
Bactoprenol monophosphates (LMPR03020006 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.000435 mg/mL	ALOGPS
logP	9.81	ALOGPS
logP	17.32	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	276.28 m³·mol^-1	ChemAxon
Polarizability	108.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Water + Undecaprenyl diphosphate > Hydrogen ion + Phosphate + Undecaprenyl phosphate
Undecaprenyl phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine > Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-monophosphate
core oligosaccharide lipid A + Undecaprenyl diphosphate > core oligosaccharide lipid A diphosphate + Undecaprenyl phosphate
Undecaprenyl phosphate + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose > Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose + Uridine 5'-diphosphate
core oligosaccharide lipid A + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose > 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A + Undecaprenyl phosphate
Uridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate
Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-N-Acetyl-D-mannosaminouronate <> Hydrogen ion + Undecaprenyl phosphate + Uridine 5'-diphosphate

Pathways:

Not Available

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
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

Links

External Links:

Resource	Link
CHEBI ID	16141
HMDB ID	Not Available
Pubchem Compound ID	5280338
Kegg ID	C00348
ChemSpider ID	4444049
Wikipedia ID	Not Available
BioCyc ID	C55-PP-GLCNAC-MANNACA
EcoCyc ID	C55-PP-GLCNAC-MANNACA

Undecaprenyl phosphate (PAMDB001054)

Structure for Undecaprenyl phosphate (PAMDB001054)