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Record Information
Version3.6
Creation Date2006-08-13 08:22:14 UTC
Update Date2016-02-11 01:06:31 UTC
HMDB IDHMDB03976
Secondary Accession Numbers
  • HMDB06329
Metabolite Identification
Common NameD-Glucuronic acid 1-phosphate
DescriptionD-Glucuronic acid 1-phosphate is an end product of the UDP-glucuronic acid pathway. Formation of free glucuronic acid from UDP-glucuronic acid can be considered as the first step in the synthesis of vitamin C, a pathway that occurs in most vertebrates, although not in guinea pigs and primates, including humans. Free glucuronic acid can also be converted to pentose phosphate intermediates via the 'pentose pathway'. The latter is interrupted in subjects with pentosuria, who have a deficiency in l-xylulose reductase (EC 1.1.1.10, an enzyme that belongs to the short-chain dehydrogenase/reductase family) and excrete abnormal amounts of l-xylulose. Some xenobiotics stimulate the formation of vitamin C in animals and enhance the excretion of l-xylulose in humans with pentosuria and have shown that aminopyrine, metyrapone and other xenobiotics cause an almost instantaneous increase in the conversion of UDP-glucuronic acid to glucuronic acid. It is usually stated that glucuronic acid formation from UDP-glucuronic acid is the result of two successive reactions comprising the hydrolysis of UDP-glucuronic acid to glucuronic acid 1-phosphate and UMP by nucleotide pyrophosphatase (E-NPP3, EC 3.6.1.9), followed by dephosphorylation of glucuronic acid 1-phosphate. Glucuronidation is responsible for conjugating potentially toxic lipophilic compounds with glucuronic acid, thereby producing molecules with greater aqueous solubility that is excreted more readily into urine and bile. The rate at which any compound may be glucuronidated depends on the concentration and activity of the UDP-glucuronosyltransferases as well as the concentration of the cofactor UDP-glucuronic acid. UDP-glucuronic acid is formed after oxidation of UDP-glucose by UDP-glucose dehydrogenase (UGDH, EC 1.1.1.22) with NAD as the electron acceptor. UDP-glucuronic acid may then be either used as the glucuronic acid donor for xenobiotic conjugation reactions by UDPglucuronosyltransferases (GlcAT-P, EC 2.4.1.17), or degraded to D-glucuronic acid 1-phosphate after the phosphodiester bond is cleaved by E-NPP3. E-NPP3 is the same enzyme that further reduces D-Glucuronic acid 1-phosphate to free D-glucuronic acid. Decreases in UDP-glucuronic acid concentration may be due to reduced availability of UDP-glucose or decreased UGDH activity or to increased activities of GlcAT-P or E-NPP3. Exposure to volatile anesthetics reduces hepatic UDP-glucuronic acid concentrations, and alters the rate of conjugation of compounds such as acetaminophen, bilirubin, diethylstilbestrol, iopanoic acid and valproic acid in a non-sex-dependent fashion in experimental mice. The depletion of UDP-glucuronic acid by anesthetics is caused by altered activity of microsomal E-NPP3. (PMID: 2167093 , 16689937 , 1276 ).
Structure
Thumb
Synonyms
ValueSource
1-O-phosphono-D-Glucopyranuronic acidHMDB
1-O-phosphono-delta-Glucopyranuronic acidHMDB
1-phospho-a-D-GlucuronateHMDB
1-phospho-alpha-delta-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-delta-Glucopyranuronic acid 1-phosphateHMDB
alpha-delta-Glucuronate 1-phosphateHMDB
alpha-delta-Glucuronic acid 1-phosphateHMDB
D-Glucuronate 1-phosphateHMDB
D-Glucuronate-1-PHMDB
D-Glucuronate-1-phosphateHMDB
delta-Glucuronate 1-phosphateHMDB
delta-Glucuronate-1-PHMDB
delta-Glucuronate-1-phosphateHMDB
delta-Glucuronic acid 1-phosphateHMDB
Glucuronate-1-PHMDB
Glucuronate-1-phosphateHMDB
Glucuronic acid 1-phosphateHMDB
Chemical FormulaC6H11O10P
Average Molecular Weight274.1193
Monoisotopic Molecular Weight274.008983084
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid
Traditional Nameglucuronic acid 1-phosphate
CAS Registry Number13168-11-1
SMILES
O[C@@H]1[C@@H](O)C(OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=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 KeyInChIKey=AIQDYKMWENWVQJ-AQKNRBDQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glucuronic acid derivatives. These 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Monosaccharide phosphate
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Monoalkyl phosphate
  • Beta-hydroxy acid
  • Alkyl phosphate
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.441Not Available
Predicted Properties
PropertyValueSource
Water Solubility33.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.66 m3·mol-1ChemAxon
Polarizability20.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023278
KNApSAcK IDNot Available
Chemspider ID389532
KEGG Compound IDC05385
BioCyc IDNot Available
BiGG ID45711
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03976
Metagene LinkHMDB03976
METLIN IDNot Available
PubChem Compound440650
PDB IDNot Available
ChEBI ID35145
References
Synthesis ReferenceHeeres, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [2167093 ]
  2. 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. [16689937 ]
  3. 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. [1276 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215