Showing Metabocard for UTP (BASm0002181)

Common NameUtp
DescriptionUridine triphosphate, also known as 5'-UTP or UTP, belongs to the class of organic compounds known as pyrimidine ribonucleoside triphosphates. These are pyrimidine ribobucleotides with triphosphate group linked to the ribose moiety. More specifically, UTP is a pyrimidine nucleoside triphosphate, consisting of the organic base uracil linked to the 1′ carbon of the ribose sugar, and esterified with tri-phosphoric acid at the 5′ position. Uridine triphosphate exists in all living species, ranging from bacteria to plants to humans. The main role of UTP is as substrate for the synthesis of RNA during transcription. UTP is the precursor for the production of CTP via the enzyme known as CTP Synthetase. UTP can be biosynthesized from UDP by the enzyme known as nucleoside diphosphate kinase by using phosphate group from ATP. UTP also has the role of a source of energy or an activator of substrates in a variety of metabolic reactions. For instance UTP can be used to activate Glucose-1-phosphate, leading to the formation of UDP-glucose and inorganic phosphate. The resulting UDP-glucose can be used in the synthesis of glycogen. UTP is also used in the metabolism of galactose, where the activated form of galactose, called UDP-galactose can be converted to UDP-glucose. UDP-glucuronate, another product of UTP reacting with glucuronic acid, is a sugar used in the creation of polysaccharides and is an intermediate in the biosynthesis of ascorbic acid (except in primates and guinea pigs).
Structure
Molecular FormulaC9H15N2O15P3
Average Mass484.14110
Monoisotopic Mass483.96853
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](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}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number63-39-8
SMILESO=c1ccn([C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1
InChI IdentifierInChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
InChI KeyPGAVKCOVUIYSFO-XVFCMESISA-N
CHEBI IDCHEBI:46398
HMDB IDHMDB0000285
Pathways
NameSMPDB/PathBank
Pyrimidine metabolism
Nucleotide Sugars Metabolism
Transcription/Translation
Galactose Metabolism
Amino Sugar Metabolism
Starch and Sucrose Metabolism
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
Azithromycin Action Pathway
Clarithromycin Action Pathway
Clindamycin Action Pathway
Erythromycin Action Pathway
Roxithromycin Action Pathway
Telithromycin Action Pathway
Amikacin Action Pathway
Gentamicin Action Pathway
Kanamycin Action Pathway
Neomycin Action Pathway
Netilmicin Action Pathway
Spectinomycin Action Pathway
Streptomycin Action Pathway
Clomocycline Action Pathway
Demeclocycline Action Pathway
Doxycycline Action Pathway
Minocycline Action Pathway
Oxytetracycline Action Pathway
Tetracycline Action Pathway
Lymecycline Action Pathway
Tay-Sachs Disease
Lactose Synthesis
DNA Replication Fork
Galactosemia II (GALK)
Galactosemia III
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
Congenital disorder of glycosylation CDG-IId
GLUT-1 deficiency syndrome
Lamivudine Metabolism Pathway
Tobramycin Action Pathway
Tigecycline Action Pathway
Arbekacin Action Pathway
Paromomycin Action Pathway
Rolitetracycline Action Pathway
Methacycline Action Pathway
Lincomycin Action Pathway
Chloramphenicol Action Pathway
Troleandomycin Action Pathway
Josamycin Action Pathway
StateSolid
Water Solubility8.37e+00 g/l
logP-0.07
logS-1.76
pKa (Strongest Acidic)0.90
pKa (Strongest Basic)-3.66
Hydrogen Acceptor Count12
Hydrogen Donor Count7
Polar Surface Area258.92 Ų
Rotatable Bond Count8
Physiological Charge-3
Formal Charge0
Refractivity85.18 m³·mol⁻¹
Polarizability35.37

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