UDP-N-acetyl-α-D-mannosamine (PAMDB110513)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110513
Identification
Name: UDP-N-acetyl-α-D-mannosamine
Description:A UDP-N-acetyl-D-mannosamine(2−) in which the anomeric centre of the pyranose fragment has α-configuration.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • uridine diphosphate N-acetylmannosamine
  • uridine 5'-(trihydrogen diphosphate)
  • P'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester
  • UDP-acetylmannosamine
  • UDP-ManNAc
Chemical Formula: C17H25N3O17P2
Average Molecular Weight: 605.34
Monoisotopic Molecular Weight: 607.081569478
InChI Key: LFTYTUAZOPRMMI-ZYQOOJPVSA-L
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)/p-2/t7-,8-,10+,11-,12-,13-,14-,15-,16-/m1/s1
CAS number: Not Available
IUPAC Name:thymidine 5'-[3-(2-acetamido-2-deoxy-α-D-mannopyranosyl) diphosphate]
Traditional IUPAC Name: {[(2S,3R,4S,5S)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3R,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
SMILES:CC(=O)NC3(C(O)C(O)C(CO)OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))3)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
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 Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.4 mg/mLALOGPS
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.41 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m3·mol-1ChemAxon
Polarizability51.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-N-acetyl-α-D-mannosamine + NAD+ + Water → UDP-N-acetyl-α-D-mannosaminouronate + NADH + Hydrogen ion
Pathways:
  • UDP-N-acetyl-α-D-mannosaminouronate biosynthesisPWY-7335
    Spectra
    Spectra: Not Available
    References
    References:
    • Samuel J, Tanner ME (2004)Active site mutants of the "non-hydrolyzing" UDP-N-acetylglucosamine 2-epimerase from Escherichia coli. Biochimica et biophysica acta 1700, Pubmed: 15210128
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI68623
    HMDBHMDB13112
    IAF126036973
    KEGGC01170
    PubChem25245190