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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	ECMDB21294
Identification
Name:	UDP-N-Acetyl-D-mannosaminouronate
Description	UDP-n-acetyl-D-mannosaminouronate is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8a174848> Close
Synonyms:	UDP-N-acetyl-D-mannosaminouronate UDP-N-acetyl-D-mannosaminouronic-acid UDP-N-acetyl-mannosaminouronic acid UDP-ManNAcA UDP-ManNAcUA UDP-N-Acetyl-2-amino-2-deoxy-D-mannuronate UDP-N-Acetyl-2-amino-2-deoxy-D-mannuronic acid UDP-N-Acetyl-D-mannosaminouronate UDP-N-Acetyl-D-mannosaminouronic acid UDP-N-Acetyl-D-mannosaminouronic-acid UDP-N-Acetyl-D-mannosaminuronate UDP-N-Acetyl-D-mannosaminuronic acid UDP-N-Acetyl-mannosaminouronate UDP-N-Acetyl-mannosaminouronic acid Uridine 5'-[3-(2-acetamido-2-deoxy-D-mannopyranosyluronate) dihydrogen diphosphate] Uridine 5'-[3-(2-acetamido-2-deoxy-D-mannopyranosyluronic acid) dihydrogen diphosphate] Uridine 5'-[3-(2-acetamido-2-deoxy-D-mannopyranosyluronic acid) dihydrogen diphosphoric acid]
Chemical Formula:	C17H22N3O18P2
Weight:	Average: 618.3134 Monoisotopic: 618.037358939
InChI Key:	DZOGQXKQLXAPND-XHUKORKBSA-K
InChI:	InChI=1S/C17H25N3O18P2/c1-5(21)18-8-10(24)11(25)13(15(27)28)36-16(8)37-40(32,33)38-39(30,31)34-4-6-9(23)12(26)14(35-6)20-3-2-7(22)19-17(20)29/h2-3,6,8-14,16,23-26H,4H2,1H3,(H,18,21)(H,27,28)(H,30,31)(H,32,33)(H,19,22,29)/p-3/t6-,8+,9-,10-,11+,12-,13+,14-,16-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2S,3S,4R,5S,6R)-6-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4-dihydroxy-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
Traditional IUPAC Name:	(2S,3S,4R,5S,6R)-6-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3,4-dihydroxy-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
SMILES:	[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O)[C@]([H])(O)[C@]2([H])N=C(C)[O-])O[C@@]([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 nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pyrimidine ribonucleoside diphosphates Pentose phosphates N-acyl-alpha-hexosamines Glycosylamines Monosaccharide phosphates Organic pyrophosphates Beta hydroxy acids and derivatives Pyrimidones Alkyl phosphates Hydropyrimidines Pyrans Oxanes Acetamides Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Lactams Secondary carboxylic acid amides Ureas Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Carboxylic acids Hydrocarbon derivatives Carbonyl compounds Organic oxides Organopnictogen compounds Organonitrogen compounds Organic anions
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Pentose-5-phosphate Pentose phosphate N-acyl-alpha-hexosamine Glycosyl compound N-glycosyl compound Monosaccharide phosphate Organic pyrophosphate Beta-hydroxy acid Pyrimidone Hydropyrimidine Phosphoric acid ester Pyran Hydroxy acid Organic phosphoric acid derivative Alkyl phosphate Oxane Monosaccharide Pyrimidine Tetrahydrofuran Vinylogous amide Acetamide Heteroaromatic compound Carboxamide group Lactam Urea Secondary carboxylic acid amide Secondary alcohol Carboxylic acid derivative Organoheterocyclic compound Azacycle Oxacycle Monocarboxylic acid or derivatives Carboxylic acid Alcohol Carbonyl group Hydrocarbon derivative Organic oxide Organopnictogen compound Organic oxygen compound Organic nitrogen compound Organonitrogen compound Organooxygen compound Organic anion Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	UDP-N-acetyl-D-mannosaminouronate(3-) (CHEBI:70731 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 29.3 g/L ALOGPS logP -1.1 ALOGPS logP -3.8 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.72 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 332.95 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 150.21 m³·mol⁻¹ ChemAxon Polarizability 49.78 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:	Water + 2 NAD + UDP-N-Acetyl-D-mannosamine <>3 Hydrogen ion +2 NADH + UDP-N-Acetyl-D-mannosaminouronate UDP-N-Acetyl-D-mannosaminouronate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate > Hydrogen ion + Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate UDP-N-Acetyl-D-mannosamine + 2 NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate +2 NADH +2 Hydrogen ion Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-N-Acetyl-D-mannosaminouronate <> Hydrogen ion + Undecaprenyl phosphate + Uridine 5'-diphosphate UDP-N-Acetyl-D-mannosamine + NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate + NADH + Hydrogen ion UDP-N-Acetyl-D-mannosamine + 2 NAD + Water > UDP-N-Acetyl-D-mannosaminouronate +2 NADH
SMPDB Pathways:	Not Available
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520
EcoCyc Pathways:	enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0000009000-0e0dc83d33c048f828f6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0gb9-0001009000-d57e00c9bf5410d64e0f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0fkc-9850106000-59521796cef414ebc854 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0uxr-8900015000-9f5688b0f34abec1f175 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01bi-9300001000-ff63898b04a88af06a61 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a7l-9500000000-e8308eea3a24b03201ed 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:	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 28581 HMDB ID Not Available Pubchem Compound ID 25246192 Kegg ID C06240 ChemSpider ID 26331255 Wikipedia ID Not Available BioCyc ID UDP-MANNACA EcoCyc ID UDP-MANNACA

Enzymes