Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB001760
Identification
Name: undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose
Description:The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Structure
Thumb
Synonyms:
  • Undecaprenyl phosphoric acid-4-amino-4-deoxy-L-arabinose
  • Undecaprenyl-P-Ara4N
Chemical Formula: C60H100NO7P
Average Molecular Weight: 978.4123
Monoisotopic Molecular Weight: 977.723741071
InChI Key: BAFPKKRTAQMYMS-MEKAZKDWSA-N
InChI:InChI=1S/C60H100NO7P/c1-46(2)23-13-24-47(3)25-14-26-48(4)27-15-28-49(5)29-16-30-50(6)31-17-32-51(7)33-18-34-52(8)35-19-36-53(9)37-20-38-54(10)39-21-40-55(11)41-22-42-56(12)43-44-67-69(64,65)68-60-59(63)58(62)57(61)45-66-60/h23,25,27,29,31,33,35,37,39,41,43,57-60,62-63H,13-22,24,26,28,30,32,34,36,38,40,42,44-45,61H2,1-12H3,(H,64,65)/b47-25+,48-27+,49-29-,50-31-,51-33-,52-35-,53-37-,54-39-,55-41-,56-43-/t57-,58-,59+,60-/m0/s1
CAS number: Not Available
IUPAC Name:{[(2S,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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})phosphinic acid
Traditional IUPAC Name: [(2S,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxyphosphinic acid
SMILES:N[C@H]1CO[C@@H](OP(=O)(O)OC\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)CCC=C(C)C)[C@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis 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 ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassPolyprenols
Direct Parent Bactoprenol monophosphates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol monophosphate
  • Amino sugar
  • Isoprenoid phosphate
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Saccharide
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000627 mg/mLALOGPS
logP8.81ALOGPS
logP14.79ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)8.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.47 Å2ChemAxon
Rotatable Bond Count35ChemAxon
Refractivity304.12 m3·mol-1ChemAxon
Polarizability118.55 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways:
  • Cationic antimicrobial peptide (CAMP) resistance pae01503
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0100000894-a62e4dc8a103905f4d8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0120111910-e5be9e4a54da58d44c1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-2221111941-6925e6aa7771c0cfc240View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-9120000035-8d6d886c52b836b2e088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9110000110-cb3862fc766b0b27c830View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2332a6d3e0faeea8875cView in MoNA
References
References:
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID60463
HMDB IDNot Available
Pubchem Compound ID44229076
Kegg IDC16157
ChemSpider ID26331957
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Catalyzes the deformylation of 4-deoxy-4-formamido-L- arabinose-phosphoundecaprenol to 4-amino-4-deoxy-L-arabinose- phosphoundecaprenol. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides (Probable)
Gene Name:
arnD
Locus Tag:
PA3555
Molecular weight:
32.9 kDa
Reactions
4-deoxy-4-formamido-beta-L-arabinose di-trans,poly-cis-undecaprenyl phosphate + H(2)O = 4-amino-4-deoxy-alpha-L-arabinose di-trans,poly-cis-undecaprenyl phosphate + formate.

Transporters

General function:
Carbohydrate transport and metabolism
Specific function:
Translocates 4-amino-4-deoxy-L-arabinose- phosphoundecaprenol (alpha-L-Ara4N-phosphoundecaprenol) from the cytoplasmic to the periplasmic side of the inner membrane
Gene Name:
arnE
Locus Tag:
PA3557
Molecular weight:
12.5 kDa
General function:
Carbohydrate transport and metabolism
Specific function:
Translocates 4-amino-4-deoxy-L-arabinose- phosphoundecaprenol (alpha-L-Ara4N-phosphoundecaprenol) from the cytoplasmic to the periplasmic side of the inner membrane
Gene Name:
arnF
Locus Tag:
PA3558
Molecular weight:
14.3 kDa