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Record Information
Version	2.0
Creation Date	2012-05-31 14:32:54 -0600
Update Date	2015-09-17 15:41:49 -0600
Secondary Accession Numbers	ECMDB20202
Identification
Name:	UDP-N-Acetyl-D-mannosamine
Description	UDP-N-acetyl-D-mannosamine 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:0xa36286c8> Close
Synonyms:	UDP-Acetylmannosamine UDP-ManNAc Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) ester Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester Uridine diphosphate N-acetylmannosamine Uridine diphosphate N-acetylgalactosamine Uridine diphosphate N-acetylmannosamine Uridine diphosphoric acid N-acetylgalactosamine Uridine diphosphoric acid N-acetylmannosamine Uridine diphosphoric acid n-acetylmannosamine Uridine-diphosphate-n-acetylgalactosamine Uridine-diphosphate-n-acetylglucosamine Uridine-diphosphoric acid-N-acetylgalactosamine Uridine-diphosphoric acid-N-acetylglucosamine
Chemical Formula:	C17H27N3O17P2
Weight:	Average: 607.3537 Monoisotopic: 607.081569477
InChI Key:	LFTYTUAZOPRMMI-IUPDHGCPSA-N
InChI:	InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10+,11-,12-,13-,14-,15-,16?/m0/s1
CAS number:	26575-17-7
IUPAC Name:	N-[(3S,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
Traditional IUPAC Name:	N-[(3S,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
SMILES:	CC(=O)N[C@@H]1[C@H](O)[C@@H](O)[C@H](CO)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)N1C=CC(=O)NC1=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 Monoalkyl phosphates Pyrimidones Hydropyrimidines Oxanes Tetrahydrofurans Acetamides Heteroaromatic compounds Vinylogous amides Secondary alcohols Secondary carboxylic acid amides Ureas Lactams Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Primary alcohols
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Pentose phosphate Pentose-5-phosphate N-acyl-alpha-hexosamine 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 Acetamide Tetrahydrofuran Heteroaromatic compound Urea Secondary carboxylic acid amide Secondary alcohol Carboxamide group Lactam Azacycle Carboxylic acid derivative Oxacycle Organoheterocyclic compound Organopnictogen compound Organooxygen compound Alcohol Primary alcohol Organic nitrogen compound Organic oxygen compound Organic oxide Carbonyl group Hydrocarbon derivative Organonitrogen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	UDP-amino sugar (CHEBI:16287 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 13 g/L ALOGPS logP -1.7 ALOGPS logP -4.1 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 307.39 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 118.4 m³·mol⁻¹ ChemAxon Polarizability 50.85 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:	Uridine diphosphate-N-acetylglucosamine <> UDP-N-Acetyl-D-mannosamine Water + 2 NAD + UDP-N-Acetyl-D-mannosamine <>3 Hydrogen ion +2 NADH + UDP-N-Acetyl-D-mannosaminouronate UDP-N-Acetyl-D-mannosamine + 2 NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate +2 NADH +2 Hydrogen ion UDP-N-Acetyl-D-mannosamine + NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate + NADH + Hydrogen ion Uridine diphosphate-N-acetylglucosamine > UDP-N-Acetyl-D-mannosamine UDP-N-Acetyl-D-mannosamine + 2 NAD + Water > UDP-N-Acetyl-D-mannosaminouronate +2 NADH Uridine diphosphate-N-acetylglucosamine <> UDP-N-acetyl-D-mannosamine + UDP-N-Acetyl-D-mannosamine UDP-N-acetyl-D-mannosamine + 2 NAD + Water + UDP-N-Acetyl-D-mannosamine > UDP-N-acetyl-α-D-mannosaminuronate +2 NADH +3 Hydrogen ion
SMPDB Pathways:	Amino sugar and nucleotide sugar metabolism I PW000886
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520 Metabolic pathways eco01100
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 splash10-03di-0910020000-206daff4fcbabb7000d9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-2921000000-3efb6b3d3ace54161746 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-4910000000-d0a8fca3f7775cdc5311 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-08g3-9701421000-d26c8c8dc5ec960bdab6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03ec-9816010000-3f9697b8af62bee7f837 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06r6-5911000000-043658d246494379ca6d View in MoNA
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 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 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
Links
External Links:	Resource Link CHEBI ID 16287 HMDB ID HMDB13112 Pubchem Compound ID 449043 Kegg ID C01170 ChemSpider ID 395672 Wikipedia ID Not Available BioCyc ID UDP-MANNAC EcoCyc ID UDP-MANNAC

Enzymes