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4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate (M2MDB003490)

Record Information
Version2.0
Creation Date2012-10-10 12:16:42 -0600
Update Date2015-06-03 17:25:55 -0600
Secondary Accession Numbers
  • ECMDB23100
Identification
Name:4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate
Description4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate is an intermediate in LPS synthesis. It is a substrate for Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase which catalyzes the reaction 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 4-amino-4-Deoxy-a-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate
  • 4-amino-4-Deoxy-a-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphoric acid
  • 4-amino-4-Deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphoric acid
  • 4-amino-4-Deoxy-α-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate
  • 4-amino-4-Deoxy-α-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphoric acid
  • UDP-Ara4FN
Chemical Formula:C61H100NO8P
Weight:Average: 1006.4224
Monoisotopic: 1005.718655693
InChI Key:KDTATMYQJZYGGT-CRHUQJHVSA-N
InChI:InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-/t58-,59-,60+,61-/m0/s1
CAS number:Not Available
IUPAC Name:N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-{[hydroxy({[(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})phosphoryl]oxy}oxan-3-yl]carboximidic acid
Traditional IUPAC Name:N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-({hydroxy[(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]oxyphosphoryl}oxy)oxan-3-yl]carboximidic acid
SMILES:OC=N[C@@]1([H])CO[C@@]([H])(OP(O)(=O)OC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@@](O)([H])[C@]1(O)[H]
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
  • Dialkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00075 g/LALOGPS
logP9.18ALOGPS
logP15.22ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)2.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area138.04 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity309.59 m³·mol⁻¹ChemAxon
Polarizability116.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
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
4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate > lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate
2 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + (KDO)2-lipid A >2 di-trans,octa-cis-undecaprenyl diphosphate + L-Ara4N-modified KDO2-Lipid A
SMPDB Pathways:
polymyxin resistancePW002052 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1100000795-cfc43b861a5ee8ffbd62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000000900-aa8f4721c04ca5ab337dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2200000930-3b10aad6c30762fed06aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-9410000021-4c5722c0f49ce0082a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9030000111-febe9824a60d18b93b15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-75958bc230996b65f282View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID53028
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDC16156
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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
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.
Protein Details
2. 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
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.