UDP-L-iduronate (CHEM040768)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:31:56 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040768
Identification
Common NameUDP-L-iduronate
ClassSmall Molecule
DescriptionA UDP-L-iduronate in which the anomeric centre of the sugar component has beta-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
UDP-L-Iduronic acidGenerator
UDP-Glucuronic acidHMDB
UDP-b-L-IduronateGenerator
UDP-b-L-Iduronic acidGenerator
UDP-beta-L-IduronateGenerator
UDP-Β-L-iduronateGenerator
UDP-Β-L-iduronic acidGenerator
Chemical FormulaC15H22N2O18P2
Average Molecular Mass580.285 g/mol
Monoisotopic Mass580.034 g/mol
CAS Registry NumberNot Available
IUPAC Name(2R,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3S,4S,5R,6R)-6-[({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILESO[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
InChI IdentifierInChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11-,12-,14-/m1/s1
InChI KeyHDYANYHVCAPMJV-NTWGTYGRSA-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
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Monoalkyl phosphate
  • Pyrimidone
  • Hydropyrimidine
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Urea
  • Lactam
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility18.1 g/LALOGPS
logP-1.2ALOGPS
logP-4.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area308.61 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.32 m³·mol⁻¹ChemAxon
Polarizability45.14 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, Positivesplash10-0w29-3322930000-0ce18416678ea80bec67Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009i-6222925000-2fe6323959ffef31a282Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("UDP-L-iduronate,1TMS,#1" TMS) - 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_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-1e6ffaa5a5ce0874c952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4911000000-15ed26bead1c905551e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-2f5aaa01239a87e8ea45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03g3-4502290000-4f7ce7e1f9b4eebe1216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ec-9605020000-2d710d0bd9ce2bdec018Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i3-4901000000-e4482078a9a42b9b8cabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1700490000-7f9159b24d34e9358740Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4921760000-cd1fe2a62f343b8eb5baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0209-6940100000-aa916ad8a0ed15e6eb2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001090000-c773521e9e340d5e6564Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-055e-9424840000-deea5ee6888efff36f31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-3936510000-b41af0ea55c95b9da1e1Spectrum
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
1D NMR13C 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 IDHMDB0012304
FooDB IDFDB028927
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-223
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30791427
ChEBI ID88243
PubChem Compound ID15592259
Kegg Compound IDC02330
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dumbrava VA, Pall ML: Control of nucleotide and erythroascorbic acid pools by cyclic AMP in Neurospora crassa. Biochim Biophys Acta. 1987 Dec 7;926(3):331-8.
2. Ward JB, Curtis CA: The biosynthesis and linkage of teichuronic acid to peptidoglycan in Bacillus licheniformis. Eur J Biochem. 1982 Feb;122(1):125-32.
3. Chowdhury JR, Jansen PL, Fischberg EB, Daniller A, Arias IM: Hepatic conversion of bilirubin monoglucuronide to diglucuronide in uridine diphosphate-glucuronyl transferase-deficient man and rat by bilirubin glucuronoside glucuronosyltransferase. J Clin Invest. 1978 Jul;62(1):191-6.
4. Marselos M, Lang M, Torronen R: Modifications of drug metabolism by disulfiram and diethyldithiocarbamate. II. D-Glucuronic acid pathway. Chem Biol Interact. 1976 Nov;15(3):277-87.
5. Kyossev ZN, Drake RR, Kyosseva SV, Elbein AD: Synthesis of a new photoaffinity probe, 5-azido-[32P]UDPxylose, by UDPglucuronate carboxylyase from wheat germ. Eur J Biochem. 1995 Feb 15;228(1):109-12.
6. Fournel S, Gregoire B, Magdalou J, Carre MC, Lafaurie C, Siest G, Caubere P: Inhibition of bilirubin UDPglucuronosyltransferase activity by triphenylacetic acid and related compounds. Biochim Biophys Acta. 1986 Sep 4;883(2):190-6.
7. Delzenne NM, Verbeeck RK: [Interactions of food and drug metabolism]. J Pharm Belg. 2001 Mar-Apr;56(2):33-7.
8. Batt AM, MacKenzie P, Hanninen O, Vainio H: Glucuronidation of 3-hydroxybenzo(a)pyrene in liver microsomes. Med Biol. 1979 Oct;57(5):281-6.
9. Puhakainen E, Hanninen O: Pyrophosphatase and glucuronosyltransferase in microsomal UDPglucuronic-acid metabolism in the rat liver. Eur J Biochem. 1976 Jan 2;61(1):165-9.
10. Brunner G, Holloway CJ: The capillary-isotachophoretic analysis of reactants and products of glucuronidation. A new method for the assay of UDPGlucuronosyltransferase. Hoppe Seylers Z Physiol Chem. 1980 Jan;361(1):1-7.
11. Zakim K, Vessey DA: Regulation of microsomal enzymes by phospholipids. IX. Production of uniquely modified forms of microsomal UDP-glucuronyltransferase by treatment with phospholipase A and detergents. Biochim Biophys Acta. 1975 Nov 20;410(1):61-73.
12. Ashurst SW, Mehta R, Cohen GM: Importance of conjugation reactions in determining the qualitative nature of polycyclic aromatic hydrocarbon-DNA interactions. Med Biol. 1979 Oct;57(5):313-20.
13. Franzen JS, Marchetti PS, Lockhart AH, Feingold DS: Special effects of UDP-sugar binding to bovine liver uridine diphosphoglucose dehydrogenase. Biochim Biophys Acta. 1983 Aug 16;746(3):146-53.
14. Ordman AB, Kirkwood S: UDPglucose dehydrogenase. Kinetics and their mechanistic implications. Biochim Biophys Acta. 1977 Mar 15;481(1):25-32.
15. Czygan P, Stiehl A, Senn M: The synthesis of bile acid glucuronides by agarose-bound UDP-glucuronyltransferase. Biochim Biophys Acta. 1980 Aug 11;619(2):228-34.
16. Pagni M, Lazarevic V, Soldo B, Karamata D: Assay for UDPglucose 6-dehydrogenase in phosphate-starved cells: gene tuaD of Bacillus subtilis 168 encodes the UDPglucose 6-dehydrogenase involved in teichuronic acid synthesis. Microbiology. 1999 May;145 ( Pt 5):1049-53.
17. Hallinan T, Pohl KR, de Brito R: Studies on the inhibition of hepatic microsomal glucuronidation by uridine nucleotides or adenosine triphosphate. Med Biol. 1979 Oct;57(5):269-73.
18. Fyffe J, Dutton GJ: Induction of UDPglucose dehydrogenase during development, organ culture, and exposure to phenobarbital. Its relation to levels of UDPglucuronic acid and overall glucuronidation in chicken and mouse. Biochim Biophys Acta. 1975 Nov 10;411(1):41-9.
19. Puhakainen E, Saarinen A, Hanninen O: UDPglucuronic acid pyrophosphatase assay with the aid of alkaline phosphatase. Acta Chem Scand B. 1977 Mar;B31(2):125-9.