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Human Metabolome Database Version 3.5

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Showing metabocard for UDP-L-rhamnose (HMDB12305)

Record Information
Version 3.5
Creation Date 2009-04-06 10:22:40 -0600
Update Date 2013-02-08 17:28:45 -0700
HMDB ID HMDB12305
Secondary Accession Numbers None
Metabolite Identification
Common Name UDP-L-rhamnose
Description UDP-L-rhamnose is synthesized from UDP-D-glucose.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Galactose-Uridine-5'-Diphosphate
  2. GDU
  3. Glucose-Uridine-C1,5'-Diphosphate
  4. UDP Galactose
  5. UDP-alpha-D-Galactose
  6. UDP-D-Galactopyranose
  7. UDP-D-Galactose
  8. UDP-Gal
  9. UDP-Galactopyranose
  10. UDP-Galactose
  11. Udpgal
  12. UPG
  13. Uridine 5'-diphosphate galactose
  14. Uridine 5'-diphosphogalactose
  15. Uridine diphosphate galactose
  16. Uridine diphosphate-D-galactose
  17. Uridine diphosphogalactose
  18. Uridine pyrophosphogalactose
  19. Uridine-5'-Diphosphate-Mannose
  20. Uridine-5'-Monophosphate Glucopyranosyl-Monophosphateester
  21. Uridinediphosphate galactose
  22. Uridinediphosphogalactose
Chemical Formula C15H24N2O16P2
Average Molecular Weight 550.3024
Monoisotopic Molecular Weight 550.060105754
IUPAC Name [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name {[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphinic acid
CAS Registry Number 1955-26-6
SMILES C[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 Identifier InChI=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 Key DRDCJEIZVLVWNC-SLBWPEPYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyrimidine Nucleotides
Sub Class Pyrimidine Nucleotide Sugars
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Pyrimidine Ribonucleoside Diphosphates
Substituents
  • 1,2 Diol
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Hydropyrimidine
  • Mixed Pentose/Hexose Disaccharide
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxane
  • Oxolane
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct Parent Pyrimidine Nucleotide Sugars
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 15.4 g/L ALOGPS
LogP -1.19 ALOGPS
LogP -3.9 ChemAxon
LogS -1.55 ALOGPS
pKa (strongest acidic) 1.73 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 13 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 271.31 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 104.91 ChemAxon
Polarizability 44.69 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028928
KNApSAcK ID Not Available
Chemspider ID 167268 Link_out
KEGG Compound ID C02199 Link_out
BioCyc ID UDP-L-RHAMNOSE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12305 Link_out
Metagene Link HMDB12305 Link_out
METLIN ID Not Available
PubChem Compound 192751 Link_out
PDB ID Not Available
ChEBI ID 17454 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Beta-1,4-galactosyltransferase 6
Reactions:
UDP-L-rhamnose + Glucosylceramide unknown Uridine 5'-diphosphate + Lactosylceramide (d18:1/24:0) details
Gene Name: B4GALT6
Uniprot ID: Q9UBX8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA