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Identification
NameUridine
Accession NumberDB02745  (EXPT03205)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number58-96-8
WeightAverage: 244.2014
Monoisotopic: 244.069536126
Chemical FormulaC9H12N2O6
InChI KeyDRTQHJPVMGBUCF-ZAKLUEHWSA-N
InChI
InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7+,8+/m0/s1
IUPAC Name
1-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)N1C=CC(=O)NC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassGlycosyl Compounds
Direct parentPyrimidine Nucleosides and Analogues
Alternative parentsPentoses; Pyrimidones; Hydropyrimidines; Tetrahydrofurans; Oxolanes; Secondary Alcohols; 1,2-Diols; Primary Alcohols; Ethers; Polyamines
Substituentspentose monosaccharide; pyrimidone; hydropyrimidine; monosaccharide; pyrimidine; oxolane; tetrahydrofuran; secondary alcohol; 1,2-diol; ether; primary alcohol; polyamine; alcohol; organonitrogen compound; amine
Classification descriptionThis compound belongs to the pyrimidine nucleosides and analogues. These are compounds comprising a pyrimidine base attached to a sugar.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
UMP Synthase Deiciency (Orotic Aciduria)DiseaseSMP00219
Beta Ureidopropionase DeficiencyDiseaseSMP00172
Dihydropyrimidinase DeficiencyDiseaseSMP00178
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)DiseaseSMP00202
Pyrimidine MetabolismMetabolicSMP00046
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8393
Blood Brain Barrier + 0.7679
Caco-2 permeable - 0.9175
P-glycoprotein substrate Non-substrate 0.7892
P-glycoprotein inhibitor I Non-inhibitor 0.9424
P-glycoprotein inhibitor II Non-inhibitor 0.9027
Renal organic cation transporter Non-inhibitor 0.9446
CYP450 2C9 substrate Non-substrate 0.7272
CYP450 2D6 substrate Non-substrate 0.8801
CYP450 3A4 substrate Non-substrate 0.6225
CYP450 1A2 substrate Non-inhibitor 0.9301
CYP450 2C9 substrate Non-inhibitor 0.9626
CYP450 2D6 substrate Non-inhibitor 0.9381
CYP450 2C19 substrate Non-inhibitor 0.9462
CYP450 3A4 substrate Non-inhibitor 0.9617
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9781
Ames test Non AMES toxic 0.7868
Carcinogenicity Non-carcinogens 0.9124
Biodegradation Ready biodegradable 0.6831
Rat acute toxicity 1.6859 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9648
hERG inhibition (predictor II) Non-inhibitor 0.8724
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point165 °CPhysProp
logP-1.98HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.35e+02 g/lALOGPS
logP-1.8ALOGPS
logP-2.4ChemAxon
logS-0.26ALOGPS
pKa (strongest acidic)9.7ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count4ChemAxon
polar surface area119.33ChemAxon
rotatable bond count2ChemAxon
refractivity52.57ChemAxon
polarizability21.75ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Hidetoshi Yoshioka, Eiji Kojima, Shuji Ishida, Hiroyuki Yoshioka, Kunichika Murakami, “2’,3’-dideoxy-4-thio-uridine derivatives, process for their preparation and antivirus agents using them.” U.S. Patent US4954485, issued June, 1970.

US4954485
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00299
PubChem Compound453551
PubChem Substance46507015
ChEBI16704
ChEMBL
Therapeutic Targets DatabaseDNC001491
PharmGKBPA130230921
HETURI
WikipediaUridine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. U6 snRNA-associated Sm-like protein LSm6

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
U6 snRNA-associated Sm-like protein LSm6 P62312 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Nucleoside-specific channel-forming protein tsx

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Nucleoside-specific channel-forming protein tsx P0A927 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Transporters

1. Equilibrative nucleoside transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Equilibrative nucleoside transporter 1 Q99808 Details

References:

  1. Marce S, Molina-Arcas M, Villamor N, Casado FJ, Campo E, Pastor-Anglada M, Colomer D: Expression of human equilibrative nucleoside transporter 1 (hENT1) and its correlation with gemcitabine uptake and cytotoxicity in mantle cell lymphoma. Haematologica. 2006 Jul;91(7):895-902. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18