Showing Metabocard for UDP (BASm0003293)

Common NameUdp
DescriptionUridine 5'-diphosphate, also known as 5'-UDP, UDP or uridine diphosphoric acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. UDP is also classified as a nucleotide diphosphate. It is an ester of pyrophosphoric acid with the nucleoside uridine. UDP consists of a pyrophosphate group, a pentose sugar ribose, and the nucleobase uracil. UDP exists in all living species, ranging from bacteria to plants to humans. In mammals UDP is an important factor in glycogenesis or the formation of glycogen in the liver. Before glucose can be stored as glycogen in the liver and muscles, the enzyme UDP-glucose pyrophosphorylase forms a UDP-glucose unit by combining glucose 1-phosphate with uridine triphosphate, cleaving a pyrophosphate ion in the process. Then, the enzyme glycogen synthase combines UDP-glucose units to form a glycogen chain. UDP is also an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. UDP plays a key role in the function of Uridine 5'-diphospho-glucuronosyltransferases (UDP-glucuronosyltransferases, UGTs) which catalyze the transfer of the glucuronic acid component of UDP-glucuronic acid to a small hydrophobic molecule. UDP-Glucuronosyltransferases are responsible for the process of glucuronidation, a major part of phase II metabolism. The reaction catalyzed by UGT enzymes involves the addition of a glucuronic acid moiety to xenobiotics and is the most important pathway for the human body's elimination of the most frequently prescribed drugs. It is also the major pathway for foreign chemical (dietary, environmental, pharmaceutical) removal for most drugs, dietary substances, toxins and endogenous substances. UGT is present in humans, other animals, plants, and bacteria. Famously, UGT enzymes are not present in the genus Felis (PMID: 10862526 ) and this accounts for a number of unusual toxicities in the cat family.
Structure
Molecular FormulaC9H14N2O12P2
Average Mass404.16120
Monoisotopic Mass404.00220
IUPAC Name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2r,3s,4r,5r)-5-(2,4-dioxo-3h-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number58-98-0
SMILESO=c1ccn([C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1
InChI IdentifierInChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
InChI KeyXCCTYIAWTASOJW-XVFCMESISA-N
CHEBI IDCHEBI:58223
HMDB IDHMDB0000295
Pathways
NameSMPDB/PathBank
Pyrimidine metabolism
Starch and sucrose metabolism
Porphyrin Metabolism
Galactose Metabolism
Amino Sugar Metabolism
Starch and Sucrose Metabolism
Androgen and Estrogen Metabolism
Ibuprofen Action Pathway
Celecoxib Action Pathway
Beta Ureidopropionase Deficiency
Dihydropyrimidinase Deficiency
Galactosemia
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
Sialuria or French Type Sialuria
UMP Synthase Deficiency (Orotic Aciduria)
Salla Disease/Infantile Sialic Acid Storage Disease
Phenytoin (Antiarrhythmic) Action Pathway
Hereditary Coproporphyria (HCP)
Acute Intermittent Porphyria
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease
Porphyria Variegata (PV)
Metachromatic Leukodystrophy (MLD)
Globoid Cell Leukodystrophy
Gaucher Disease
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Tay-Sachs Disease
Codeine Action Pathway
Morphine Action Pathway
Nicotine Action Pathway
Irinotecan Action Pathway
Etoposide Action Pathway
Lactose Synthesis
Tamoxifen Action Pathway
Fabry disease
Krabbe disease
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
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
Congenital disorder of glycosylation CDG-IId
GLUT-1 deficiency syndrome
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
Lamivudine Metabolism Pathway
Artemether Metabolism Pathway
Mycophenolic Acid Metabolism Pathway
Androstenedione Metabolism
Estrone Metabolism
StateSolid
Water Solubility8.89e+00 g/l
logP-0.94
logS-1.66
pKa (Strongest Acidic)1.77
pKa (Strongest Basic)-3.66
Hydrogen Acceptor Count10
Hydrogen Donor Count6
Polar Surface Area212.39 Ų
Rotatable Bond Count6
Physiological Charge-2
Formal Charge0
Refractivity74.31 m³·mol⁻¹
Polarizability30.41

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