ChemFOnt: Showing chemical card for D-Glucuronic acid 1-phosphate (CFc000002020)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:48 UTC

Chemfont ID

CFc000002020

Molecule Identification

Common Name

D-Glucuronic acid 1-phosphate

Definition

D-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-Phosphono-D-glucopyranuronic acid	HMDB
1-Phospho-a-D-Glucuronate	HMDB
1-Phospho-alpha-D-Glucuronate	HMDB
a-D-Glucopyranuronic acid 1-phosphate	HMDB
a-D-Glucuronic acid 1-phosphate	HMDB
alpha-D-Glucuronate 1-phosphate	HMDB
alpha-D-Glucuronic acid 1-phosphate	HMDB
alpha-D-Glucopyranuronic acid 1-phosphate	HMDB
D-Glucuronate 1-phosphate	HMDB, Generator
D-Glucuronate-1-P	HMDB
D-Glucuronate-1-phosphate	HMDB
D-Glucuronic acid 1-phosphate	HMDB
Glucuronate-1-P	HMDB
Glucuronate-1-phosphate	HMDB
Glucuronic acid 1-phosphate	HMDB
D-Glucuronic acid 1-phosphoric acid	Generator
α-D-Glucopyranuronic acid 1-phosphate	HMDB
α-D-Glucuronic acid 1-phosphate	HMDB

Chemical Formula

C₆H₁₁O₁₀P

Average Molecular Weight

274.1193

Monoisotopic Molecular Weight

274.008983084

IUPAC Name

(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid

Traditional Name

glucuronic acid 1-phosphate

CAS Registry Number

13168-11-1

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 Key

AIQDYKMWENWVQJ-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

uronic acid phosphate (CHEBI:35145 )

Functional Ontology

Not Available

Placenta (HMDB: HMDB0003976)

Source

Endogenous

Endogenous (HMDB: HMDB0003976)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	33.8 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.15	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.66 m³·mol⁻¹	ChemAxon
Polarizability	20.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003976

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023278

KNApSAcK ID

Not Available

Chemspider ID

389532

KEGG Compound ID

C05385

BioCyc ID

Not Available

BiGG ID

45711

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440650

PDB ID

Not Available

ChEBI ID

35145

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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.

Showing chemical card for D-Glucuronic acid 1-phosphate (CFc000002020)

MOL for CFc000002020 (D-Glucuronic acid 1-phosphate)

3D MOL for CFc000002020 (D-Glucuronic acid 1-phosphate)

3D SDF for CFc000002020 (D-Glucuronic acid 1-phosphate)

3D-SDF for CFc000002020 (D-Glucuronic acid 1-phosphate)

PDB for CFc000002020 (D-Glucuronic acid 1-phosphate)

3D PDB for CFc000002020 (D-Glucuronic acid 1-phosphate)

SMILES for CFc000002020 (D-Glucuronic acid 1-phosphate)

INCHI for CFc000002020 (D-Glucuronic acid 1-phosphate)

Structure for CFc000002020 (D-Glucuronic acid 1-phosphate)

3D Structure for CFc000002020 (D-Glucuronic acid 1-phosphate)