UDP-L-rhamnose (CHEM040769)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:31:59 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040769
Identification
Common NameUDP-L-rhamnose
ClassSmall Molecule
DescriptionA UDP-L-rhamnose in which the rhamnose portion has beta-configuration at its anomeric centre
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Uridine 5'-(trihydrogen diphosphate), mono(6-deoxy-beta-L-mannopyranosyl) esterChEBI
Uridine 5'-(trihydrogen diphosphate), mono(6-deoxy-b-L-mannopyranosyl) esterGenerator
Uridine 5'-(trihydrogen diphosphate), mono(6-deoxy-β-L-mannopyranosyl) esterGenerator
Uridine 5'-(trihydrogen diphosphoric acid), mono(6-deoxy-b-L-mannopyranosyl) esterGenerator
Uridine 5'-(trihydrogen diphosphoric acid), mono(6-deoxy-beta-L-mannopyranosyl) esterGenerator
Uridine 5'-(trihydrogen diphosphoric acid), mono(6-deoxy-β-L-mannopyranosyl) esterGenerator
Galactose-uridine-5'-diphosphateHMDB
GDUHMDB
Glucose-uridine-C1,5'-diphosphateHMDB
UDP GalactoseHMDB
UDP-alpha-D-GalactoseHMDB
UDP-D-GalactopyranoseHMDB
UDP-D-GalactoseHMDB
UDP-GalHMDB
UDP-GalactopyranoseHMDB
UDP-GalactoseHMDB
UdpgalHMDB
UPGHMDB
Uridine 5'-diphosphate galactoseHMDB
Uridine 5'-diphosphogalactoseHMDB
Uridine diphosphate galactoseHMDB
Uridine diphosphate-D-galactoseHMDB
Uridine diphosphogalactoseHMDB
Uridine pyrophosphogalactoseHMDB
Uridine-5'-diphosphate-mannoseHMDB
Uridine-5'-monophosphate glucopyranosyl-monophosphateesterHMDB
Uridinediphosphate galactoseHMDB
UridinediphosphogalactoseHMDB
UDP-beta-L-RhamnoseMeSH, HMDB
UDP-b-L-RhamnoseGenerator
UDP-Β-L-rhamnoseGenerator
UDP-RhaMeSH
UDP-RhamnoseMeSH
Chemical FormulaC15H24N2O16P2
Average Molecular Mass550.302 g/mol
Monoisotopic Mass550.060 g/mol
CAS Registry Number1955-26-6
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy([hydroxy([(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy)phosphoryl]oxy)phosphinic acid
SMILESC[C@@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C15H24N2O16P2/c1-5-8(19)10(21)12(23)14(30-5)32-35(27,28)33-34(25,26)29-4-6-9(20)11(22)13(31-6)17-3-2-7(18)16-15(17)24/h2-3,5-6,8-14,19-23H,4H2,1H3,(H,25,26)(H,27,28)(H,16,18,24)/t5-,6+,8-,9+,10+,11+,12+,13+,14+/m0/s1
InChI KeyDRDCJEIZVLVWNC-SLBWPEPYSA-N
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine 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
  • Monoalkyl phosphate
  • Pyrimidone
  • Hydropyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Oxane
  • Phosphoric acid ester
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Lactam
  • Urea
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.4 g/LALOGPS
logP-1.2ALOGPS
logP-3.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area274.8 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.23 m³·mol⁻¹ChemAxon
Polarizability45.7 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-057l-4933450000-9b68de4de326b7782ff3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004j-7354219000-9fc893b0c5397f725ee6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("UDP-L-rhamnose,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-052b-5614390000-8207db0554e68840adcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-7af2d5ab14e05545288fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4911000000-07a3ee7bed9a9e59aa87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-74f891c988bc2c098848Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0lyn-5502290000-504031de82fe382cb81cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9604010000-1bdfc26f473d183f5612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4901000000-149a648e41231773f1fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000960000-eeec69d4e41830f15305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r90-5653950000-3e93cf6653d30c282fceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9531000000-f9dcc8cd87e605b25ce2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-2c0643b44b5b1f646668Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056v-9503430000-17e241cf1089b9364116Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2419000000-1e0a5bbc494bdb18a07aSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012305
FooDB IDFDB028928
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDUDP-L-RHAMNOSE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID167268
ChEBI ID84725
PubChem Compound ID192751
Kegg Compound IDC02199
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1898019
2. Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.
3. Qi Y, Yamauchi Y, Ling J, Kawano N, Li D, Tanaka K: Cloning of a putative monogalactosyldiacylglycerol synthase gene from rice (Oryza sativa L.) plants and its expression in response to submergence and other stresses. Planta. 2004 Jul;219(3):450-8. Epub 2004 Apr 16.
4. Sharma A, Malakar P: Structure modeling and comparative genomics for epimerase enzyme (Gal10p). Bioinformation. 2010 Nov 27;5(6):266-70.
5. Agarwal S, Mishra N, Agarwal S, Dixit A: Characterization of the active site and coenzyme binding pocket of the monomeric UDP- galactose 4'- epimerase of Aeromonas hydrophila. BMB Rep. 2010 Jun;43(6):419-26.
6. Chatterjee S, Castiglione E: UDPgalactose:glucosylceramide beta 1----4-galactosyltransferase activity in human proximal tubular cells from normal and familial hypercholesterolemic homozygotes. Biochim Biophys Acta. 1987 Jan 20;923(1):136-42.
7. Berry GT: Galactosemia: when is it a newborn screening emergency? Mol Genet Metab. 2012 May;106(1):7-11. doi: 10.1016/j.ymgme.2012.03.007. Epub 2012 Mar 21.
8. Nakahara Y, Okamoto K: Unusual properties of the prespore-specific enzyme, UDPgalactose:polysaccharide galactosyl transferase, of Dictyostelium discoideum. J Basic Microbiol. 2004;44(6):459-70.
9. Majumdar S, Ghatak J, Mukherji S, Bhattacharjee H, Bhaduri A: UDPgalactose 4-epimerase from Saccharomyces cerevisiae. A bifunctional enzyme with aldose 1-epimerase activity. Eur J Biochem. 2004 Feb;271(4):753-9.
10. Bornemann S: Flavoenzymes that catalyse reactions with no net redox change. Nat Prod Rep. 2002 Dec;19(6):761-72.