D-Glucuronic acid 1-phosphate (CHEM035611)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:55:35 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035611
Identification
Common NameD-Glucuronic acid 1-phosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-O-Phosphono-D-glucopyranuronic acidHMDB
1-Phospho-a-D-GlucuronateHMDB
1-Phospho-alpha-D-GlucuronateHMDB
a-D-Glucopyranuronic acid 1-phosphateHMDB
a-D-Glucuronic acid 1-phosphateHMDB
alpha-D-Glucuronate 1-phosphateHMDB
alpha-D-Glucuronic acid 1-phosphateHMDB
alpha-D-Glucopyranuronic acid 1-phosphateHMDB
D-Glucuronate 1-phosphateHMDB, Generator
D-Glucuronate-1-PHMDB
D-Glucuronate-1-phosphateHMDB
D-Glucuronic acid 1-phosphateHMDB
Glucuronate-1-PHMDB
Glucuronate-1-phosphateHMDB
Glucuronic acid 1-phosphateHMDB
D-Glucuronic acid 1-phosphoric acidGenerator
α-D-Glucopyranuronic acid 1-phosphateHMDB
α-D-Glucuronic acid 1-phosphateHMDB
Chemical FormulaC6H11O10P
Average Molecular Mass274.119 g/mol
Monoisotopic Mass274.009 g/mol
CAS Registry Number13168-11-1
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid
Traditional Nameglucuronic acid 1-phosphate
SMILESO[C@@H]1[C@@H](O)C(OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C6H11O10P/c7-1-2(8)4(5(10)11)15-6(3(1)9)16-17(12,13)14/h1-4,6-9H,(H,10,11)(H2,12,13,14)/t1-,2-,3+,4-,6?/m0/s1
InChI KeyAIQDYKMWENWVQJ-AQKNRBDQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Beta-hydroxy acid
  • Monoalkyl phosphate
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Alkyl phosphate
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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 Solubility33.8 g/LALOGPS
logP-1.7ALOGPS
logP-2.7ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.15ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area173.98 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.66 m³·mol⁻¹ChemAxon
Polarizability20.54 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9210000000-91503db5b551dadb9675Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000w-5593680000-6e0281d42f39758218b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9140000000-084c0e4f4c4a5be9de3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9250000000-09e248d29741aec1044eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9200000000-b3ab5301cd7a08a10824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ba-8390000000-8b3c5d20411d34f04721Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9020000000-26126d6f2f7769393410Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-75ca78f7a2ee59d6bb7fSpectrum
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 IDHMDB0003976
FooDB IDFDB023278
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45711
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389532
ChEBI ID35145
PubChem Compound ID440650
Kegg Compound IDC05385
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Heeres, Andre; Van Doren, Henk A.; Gotlieb, Kees F.; Bleeker, Ido P. Synthesis of a- and b-D-glucopyranuronate 1-phosphate and a-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch. Carbohydrate Research (1997), 299(4), 221-227.
2. Heeres, Andre; Van Doren, Henk A.; Gotlieb, Kees F.; Bleeker, Ido P. Synthesis of a- and b-D-glucopyranuronate 1-phosphate and a-D-glucopyranuronate 1-fluoride: intermediates in the synthesis of D-glucuronic acid from starch. Carbohydrate Research (1997), 299(4), 221-227.
3. Watkins JB 3rd, Engles DR, Beck LV: Effect of volatile anesthetics on the hepatic UDP-glucuronic acid pathway in mice. Biochem Pharmacol. 1990 Aug 15;40(4):731-5.
4. Linster CL, Van Schaftingen E: Glucuronate, the precursor of vitamin C, is directly formed from UDP-glucuronate in liver. FEBS J. 2006 Apr;273(7):1516-27.
5. 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.
6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.