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Record Information
Version	2.0
Creation Date	2012-10-10 12:21:53 -0600
Update Date	2015-06-03 17:26:09 -0600
Secondary Accession Numbers	ECMDB23202
Identification
Name:	UDP-beta-L-Threo-pentapyranos-4-ulose
Description	UDP-beta-L-Threo-pentapyranos-4-ulose is an intermediate in the polymixin resistance pathway. It is a substrate for the enzyme UDP-4-amino-4-deoxy-L-arabinose aminotransferase which catalyzes the reaction UDP-4-amino-4-deoxy-beta-L-arabinopyranose + 2-oxoglutarate = UDP-beta-L-threo-pentapyranos-4-ulose + L-glutamate. Some Gram-negative bacteria, specifically Salmonella typhimurium and Escherichia coli, can become resistant to polymyxin by the modification of their lipid A structure via the attachment of 4-amino-4-deoxy-L-arabinopyranose (L-Ara4N) groups to one or more phosphate groups. This addition causes an absolute increase in lipid A charge, thus lowering the affinity of positively charged polymyxins.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaea577ac> Close
Synonyms:	UDP-b-L-threo-Pentapyranos-4-ulose UDP-β-L-threo-Pentapyranos-4-ulose
Chemical Formula:	C14H20N2O16P2
Weight:	Average: 534.2599 Monoisotopic: 534.028805626
InChI Key:	URJZIQLTPCJVMW-SVROINDSSA-N
InChI:	InChI=1S/C14H20N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t6-,8+,9-,10-,11-,12?,13-/m1/s1
CAS number:	Not Available
IUPAC Name:	{[(2R,3S,4R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name:	[(2R,3S,4R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid
SMILES:	[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OCC(=O)[C@]([H])(O)[C@@]2([H])O)OC([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine ribonucleotides
Direct Parent	Pyrimidine ribonucleoside diphosphates
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates Organic pyrophosphates Pyrimidones Monoalkyl phosphates Oxanes Hydropyrimidines Tetrahydrofurans Vinylogous amides Heteroaromatic compounds Ureas Secondary alcohols Cyclic ketones Lactams Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds
Substituents	Pyrimidine ribonucleoside diphosphate Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound Monosaccharide phosphate Organic pyrophosphate Pyrimidone Monoalkyl phosphate Hydropyrimidine Monosaccharide Organic phosphoric acid derivative Oxane Phosphoric acid ester Pyrimidine Alkyl phosphate Vinylogous amide Heteroaromatic compound Tetrahydrofuran Cyclic ketone Ketone Urea Secondary alcohol Lactam Azacycle Oxacycle Organoheterocyclic compound Alcohol Organopnictogen compound Carbonyl group Organic oxide Organonitrogen compound Organooxygen compound Organic nitrogen compound Hydrocarbon derivative Organic oxygen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 20.6 g/L ALOGPS logP -1.2 ALOGPS logP -3.5 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 271.64 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 99.97 m³·mol⁻¹ ChemAxon Polarizability 42.87 ų ChemAxon Number of Rings 3 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:	Cytoplasm
Reactions:	UDP-Glucuronic acid + NAD > UDP-beta-L-Threo-pentapyranos-4-ulose + Carbon dioxide + NADH 4-Amino-4-deoxy-L-arabinose + Oxoglutaric acid > UDP-beta-L-Threo-pentapyranos-4-ulose + DL-Glutamic acid
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_5_19) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-0901110000-e0ba768f9204712325d7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3910000000-66e41dd80a3d0e769bd4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-5900000000-8e25509fbca294df0a8a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03ec-5901330000-ce4dd8c67bab9e781fb7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-06r6-6923000000-99667f74db4450385d6b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06r6-5900000000-8fe9b7c43c59211f61d3 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 25244749 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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