UDP-2-acetamido-2,6-dideoxy-α-D-xylo-hex4-ulose (PAMDB110508)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110508
Identification
Name: UDP-2-acetamido-2,6-dideoxy-α-D-xylo-hex4-ulose
Description:A doubly-charged nucleotide-sugar oxoanion arising from deprotonation of both free diphosphate OH groups of UDP-2-acetamido-2,6-dideoxy-α-D-xylo-hex-4-ulose; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-2-acetamido-2,6-dideoxy-α-D-xylo-4-hexulose
  • UDP-2-acetamido-4-dehydro-2,6-dideoxyglucose
  • N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy- tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy- phosphinoyl]oxy-4-hydroxy-6-methyl-5-oxo-tetrahydropyran-3-yl] acetamide
  • uridine 5'-[3-(2-acetamido-2-deoxy--D-xylo-hexopyranosyl-4-ulose) dihydrogen diphosphate]
Chemical Formula: C17H23N3O16P2
Average Molecular Weight: 589.0710047917
Monoisotopic Molecular Weight: 589.0710047917
InChI Key: XBILTLYIKDPORV-HZUXRPHDSA-L
InChI: InChI=1S/C17H25N3O16P2/c1-6-11(23)13(25)10(18-7(2)21)16(33-6)35-38(30,31)36-37(28,29)32-5-8-12(24)14(26)15(34-8)20-4-3-9(22)19-17(20)27/h3-4,6,8,10,12-16,24-26H,5H2,1-2H3,(H,18,21)(H,28,29)(H,30,31)(H,19,22,27)/p-2/t6-,8-,10-,12-,13-,14-,15-,16-/m1/s1
CAS number: Not Available
IUPAC Name:uridine 5'-[3-(2-acetamido-2-deoxy-α-D-xylo-hexopyranosyl-4-ulose) diphosphate]
Traditional IUPAC Name: Not Available
SMILES:CC3(C(=O)C(C(C(OP(OP(OCC1(C(C(C(O1)N2(C=CC(NC2=O)=O))O)O))([O-])=O)([O-])=O)O3)NC(C)=O)O)
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Acetamide
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Carboxamide group
  • Ketone
  • Lactam
  • Cyclic ketone
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
  • a small molecule (UDP-2-ACETAMIDO-4-DEHYDRO-26-DIDEOXYGLU)
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight587.324 g/molPubChem
XLogP3-AA-5.9 PubChem
Hydrogen Bond Donor Count5 PubChem
Hydrogen Bond Acceptor Count16 PubChem
Rotatable Bond Count9 PubChem
Exact Mass587.055 g/molPubChem
Monoisotopic Mass587.055 g/molPubChem
Topological Polar Surface Area283 A^2PubChem
Heavy Atom Count38 PubChem
Formal Charge-2 PubChem
Complexity1080 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count8 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
  • UDP-N-acetyl-α-D-fucosamine biosynthesisPWY-7333
    Spectra
    Spectra: Not Available
    References
    References:
    • Mulrooney EF, Poon KK, McNally DJ, Brisson JR, Lam JS (2005)Biosynthesis of UDP-N-acetyl-L-fucosamine, a precursor to the biosynthesis of lipopolysaccharide in Pseudomonas aeruginosa serotype O11. The Journal of biological chemistry 280, Pubmed: 15778500
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI62375
    KEGGC04613
    PubChem53239711