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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:40 UTC
Update Date2021-09-14 15:40:04 UTC
HMDB IDHMDB0012305
Secondary Accession Numbers
  • HMDB12305
Metabolite Identification
Common NameUDP-L-rhamnose
DescriptionUDP-L-rhamnose 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. UDP-L-rhamnose is found, on average, in the highest concentration within milk (cow). UDP-L-rhamnose has also been detected, but not quantified in, several different foods, such as oyster mushrooms (Pleurotus ostreatus), sweet rowanberries (Grataegosorbus mitschurinii), cumins (Cuminum cyminum), ucuhubas (Virola surinamensis), and walnuts (Juglans). This could make UDP-L-rhamnose a potential biomarker for the consumption of these foods. UDP-L-rhamnose is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on UDP-L-rhamnose.
Structure
Thumb
Synonyms
Chemical FormulaC15H24N2O16P2
Average Molecular Weight550.3024
Monoisotopic Molecular Weight550.060105754
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
CAS Registry Number1955-26-6
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 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
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028928
KNApSAcK IDNot Available
Chemspider ID167268
KEGG Compound IDC02199
BioCyc IDUDP-L-RHAMNOSE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192751
PDB IDNot Available
ChEBI ID84725
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:15088147 ]
  2. Sharma A, Malakar P: Structure modeling and comparative genomics for epimerase enzyme (Gal10p). Bioinformation. 2010 Nov 27;5(6):266-70. [PubMed:21364830 ]
  3. 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. [PubMed:20587332 ]
  4. 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. [PubMed:3099851 ]
  5. 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. [PubMed:22483615 ]
  6. 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. [PubMed:15558817 ]
  7. 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. [PubMed:14764091 ]
  8. Bornemann S: Flavoenzymes that catalyse reactions with no net redox change. Nat Prod Rep. 2002 Dec;19(6):761-72. [PubMed:12521268 ]

Enzymes

General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Required for the biosynthesis of glycosphingolipids.
Gene Name:
B4GALT6
Uniprot ID:
Q9UBX8
Molecular weight:
44913.315
Reactions
UDP-L-rhamnose + Glucosylceramide → Uridine 5'-diphosphate + LacCer(d18:1/24:0)details