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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:15 -0600
Update Date	2015-06-03 17:21:06 -0600
Secondary Accession Numbers	ECMDB21293
Identification
Name:	UDP-4-Keto-pyranose
Description	UDP-4-keto-pyranose is a member of the chemical class known as Pyrimidine Ribonucleoside Diphosphates. These are pyrimidine ribobucleotides with diphosphate group linked to the ribose moiety.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae9345c8> Close
Synonyms:	UDP-4-keto-pyranose UDP-4-Ketopentose UDP-Ara4O UDP-L-Ara4O Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphate Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphoric acid Uridine 5'-b-L-threo-pentapyranosyl-4''-ulose diphosphate Uridine 5'-b-L-threo-pentapyranosyl-4''-ulose diphosphoric acid Uridine 5'-beta-L-threo-pentapyranosyl-4''-ulose diphosphate Uridine 5'-beta-L-threo-pentapyranosyl-4''-ulose diphosphoric acid Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphate Uridine 5'-β-L-threo-pentapyranosyl-4''-ulose diphosphoric acid
Chemical Formula:	C14H18N2O16P2
Weight:	Average: 532.244 Monoisotopic: 532.013155562
InChI Key:	URJZIQLTPCJVMW-SVROINDSSA-L
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)/p-2/t6-,8+,9-,10-,11-,12?,13-/m1/s1
CAS number:	Not Available
IUPAC Name:	1-[(3R,4S,5R)-5-{[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate
Traditional IUPAC Name:	1-[(3R,4S,5R)-5-[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate
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 Organic pyrophosphates Monosaccharide phosphates Pyrimidones Oxanes Hydropyrimidines Alkyl phosphates Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Ureas Secondary alcohols Lactams Cyclic ketones Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Pyrimidine ribonucleoside diphosphate Pentose-5-phosphate Pentose phosphate N-glycosyl compound Glycosyl compound Organic pyrophosphate Monosaccharide phosphate Pyrimidone Alkyl phosphate Pyrimidine Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Hydropyrimidine Heteroaromatic compound Vinylogous amide Tetrahydrofuran Cyclic ketone Urea Secondary alcohol Lactam Ketone Oxacycle Azacycle Organoheterocyclic compound Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organooxygen compound Organonitrogen compound Carbonyl group Alcohol Organic anion 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 50.8 g/L ALOGPS logP -1.3 ALOGPS logP -3.5 ChemAxon logS -1.1 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 5 ChemAxon Polar Surface Area 277.3 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 109.4 m³·mol⁻¹ ChemAxon Polarizability 42.18 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:	L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose NAD + Uridine diphosphate glucuronic acid > Carbon dioxide + NADH + UDP-4-Keto-pyranose Uridine diphosphate glucuronic acid + NAD <> UDP-4-Keto-pyranose + Carbon dioxide + NADH + Hydrogen ion Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + Oxoglutaric acid <> UDP-4-Keto-pyranose + L-Glutamate L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose NAD + Uridine diphosphate glucuronic acid > Carbon dioxide + NADH + UDP-4-Keto-pyranose NAD + Uridine diphosphate glucuronic acid > Carbon dioxide + NADH + UDP-4-Keto-pyranose
SMPDB Pathways:	Not Available
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520
EcoCyc Pathways:	polymyxin resistance PWY0-1338
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-0200190000-d590a1d321f92c78316f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01t9-0111090000-c63a25ccd6ed116d50d3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0089-9801000000-a06ed8c72e1e5e635698 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001l-8200190000-c3435a8aa4d3d5a746bd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003s-8900080000-05ab55bc9c02e1ebbf87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-059x-9100000000-9c2450446a73c43177af View in MoNA
References
References:	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 Not Available HMDB ID Not Available Pubchem Compound ID 25244748 Kegg ID C16155 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID 5-BETA-L-THREO-PENTAPYRANOSYL-4-ULOSE- EcoCyc ID 5-BETA-L-THREO-PENTAPYRANOSYL-4-ULOSE-

Enzymes