Showing Metabocard for UDP-alpha-D-glucuronate (BASm0003165)

Common NameUdp-alpha-d-glucuronate
DescriptionUridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID:16815917 ).
Structure
Molecular FormulaC15H22N2O18P2
Average Mass580.28530
Monoisotopic Mass580.03428
IUPAC Name(2S,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(2s,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
CAS Registry Number2616-64-0
SMILESO=C([O-])[C@H]1O[C@H](OP(=O)([O-])OP(=O)([O-])OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
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-LXQIFKJMSA-N
CHEBI IDCHEBI:58052
HMDB IDHMDB0000935
Pathways
NameSMPDB/PathBank
Nucleotide Sugars Metabolism
Porphyrin Metabolism
Starch and Sucrose Metabolism
Androgen and Estrogen Metabolism
Ibuprofen Action Pathway
Celecoxib Action Pathway
Phenytoin (Antiarrhythmic) Action Pathway
Hereditary Coproporphyria (HCP)
Acute Intermittent Porphyria
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease
Porphyria Variegata (PV)
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Codeine Action Pathway
Morphine Action Pathway
Nicotine Action Pathway
Irinotecan Action Pathway
Etoposide Action Pathway
Tamoxifen Action Pathway
Galactosemia II (GALK)
Galactosemia III
Glycogen synthetase deficiency
Glycogenosis, Type III. Cori disease, Debrancher glycogenosis
Glycogenosis, Type IV. Amylopectinosis, Anderson disease
Glycogenosis, Type VI. Hers disease
Mucopolysaccharidosis VI. Sly syndrome
Sucrase-isomaltase deficiency
Aromatase deficiency
Ibuprofen Metabolism Pathway
Irinotecan Metabolism Pathway
Etoposide Metabolism Pathway
Tamoxifen Metabolism Pathway
Codeine Metabolism Pathway
Morphine Metabolism Pathway
Nicotine Metabolism Pathway
Valproic Acid Metabolism Pathway
Tramadol Metabolism Pathway
Acetaminophen Metabolism Pathway
Nevirapine Metabolism Pathway
Celecoxib Metabolism Pathway
Sorafenib Metabolism Pathway
Artemether Metabolism Pathway
Mycophenolic Acid Metabolism Pathway
Androstenedione Metabolism
Estrone Metabolism
StateSolid
Water Solubility1.81e+01 g/l
logP-1.21
logS-1.51
pKa (Strongest Acidic)1.72
pKa (Strongest Basic)-3.73
Hydrogen Acceptor Count15
Hydrogen Donor Count9
Polar Surface Area308.61 Ų
Rotatable Bond Count9
Physiological Charge-3
Formal Charge0
Refractivity106.32 m³·mol⁻¹
Polarizability45.26

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