Identification
NameUridine
Accession NumberDB02745  (EXPT03205)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIWHI7HQ7H85
CAS number58-96-8
WeightAverage: 244.2014
Monoisotopic: 244.069536126
Chemical FormulaC9H12N2O6
InChI KeyDRTQHJPVMGBUCF-XVFCMESISA-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-/m1/s1
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
U6 snRNA-associated Sm-like protein LSm6ProteinunknownNot AvailableHumanP62312 details
Nucleoside-specific channel-forming protein tsxProteinunknownNot AvailableEscherichia coli (strain K12)P0A927 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Pyrimidine MetabolismMetabolicSMP00046
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)DiseaseSMP00202
Beta Ureidopropionase DeficiencyDiseaseSMP00172
Dihydropyrimidinase DeficiencyDiseaseSMP00178
UMP Synthase Deiciency (Orotic Aciduria)DiseaseSMP00219
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Male Subjects1
1TerminatedTreatmentPGM31
2CompletedTreatment5'-Nucleotidase Syndrome1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentDepression, Bipolar2
4Not Yet RecruitingTreatmentSuicidal Ideation1
Not AvailableActive Not RecruitingNot AvailableBipolar Affective Disorders / Bipolar Disorder (BD) / Depression, Bipolar1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)165 °CPhysProp
logP-1.98HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility135.0 mg/mLALOGPS
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 Area119.33 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.57 m3·mol-1ChemAxon
Polarizability21.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8393
Blood Brain Barrier+0.7679
Caco-2 permeable-0.9175
P-glycoprotein substrateNon-substrate0.7892
P-glycoprotein inhibitor INon-inhibitor0.9424
P-glycoprotein inhibitor IINon-inhibitor0.9027
Renal organic cation transporterNon-inhibitor0.9446
CYP450 2C9 substrateNon-substrate0.7272
CYP450 2D6 substrateNon-substrate0.8801
CYP450 3A4 substrateNon-substrate0.6225
CYP450 1A2 substrateNon-inhibitor0.9301
CYP450 2C9 inhibitorNon-inhibitor0.9626
CYP450 2D6 inhibitorNon-inhibitor0.9381
CYP450 2C19 inhibitorNon-inhibitor0.9462
CYP450 3A4 inhibitorNon-inhibitor0.9617
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9781
Ames testNon AMES toxic0.7868
CarcinogenicityNon-carcinogens0.9124
BiodegradationReady biodegradable0.6831
Rat acute toxicity1.6859 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9648
hERG inhibition (predictor II)Non-inhibitor0.8724
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00kb-1970000000-d1bfa838a4e9fa77c862View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kb-1960000000-a8283468b762a8520102View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-1950000000-70fdf4785544d0968f70View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9520000000-591c0bcf8f956d710367View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-066s-2970000000-36fbef6f6b10c2895df4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1890000000-dd0569d4351a64c566c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00kb-1970000000-d1bfa838a4e9fa77c862View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00kb-1960000000-a8283468b762a8520102View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014i-1950000000-70fdf4785544d0968f70View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9520000000-591c0bcf8f956d710367View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-066s-2970000000-36fbef6f6b10c2895df4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-1890000000-dd0569d4351a64c566c9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014j-1940000000-8b7a5ce66afa9b9bf939View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00kb-1950000000-00519445de22f955367dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-7010b37007f5c3d9ce1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-3900000000-b4639c8c89eac6158da6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-022a-9200000000-f8472930d09b32f54790View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0291000000-aebaa77a411473acb859View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-9000000000-205562662b564ebdca28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-776595fd1c19f6ec51cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-10358e53c56bcb50ed4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0971000000-f989283d2dec564a3af0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00kf-9000000000-c11e7bfdec0b5c7bf450View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-104e62fbffc4110779efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-eaf6ff9ac3971d6f045fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-052f-0697120000-c9fd5b8d641165d84e92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9000000000-995de18be458c48a8d2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0590000000-4d1d6aba25697dd11da8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uki-0190000000-3aea11527d0520158d77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004l-0291010000-c8f22405e9290fccc011View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0490000000-1a2f990a874bb1868249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0090000000-c8efbe58f0df63698b2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0090000000-7495d9b948a8e3b7b83bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03dj-3960000000-3466ccfdf88139ddf140View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03di-3900000000-0d08e4a7d4b8aacee6e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-4900000000-d942ee27b3ca1d6ef94dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-9700000000-594c7bb6dc6de848ff11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-022d-9100000000-2826c4eb794745ec3148View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0910000000-617b4ec6cf749942c0cdView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative ParentsGlycosylamines / Pentoses / Pyrimidones / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Vinylogous amides / Ureas / Lactams / Secondary alcohols
SubstituentsPyrimidine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Pyrimidone / Hydropyrimidine / Monosaccharide / Pyrimidine / Vinylogous amide / Tetrahydrofuran
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsuridines (CHEBI:16704 ) / Ribonucleosides (C00299 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Poly(a) rna binding
Specific Function:
Component of LSm protein complexes, which are involved in RNA processing and may function in a chaperone-like manner, facilitating the efficient association of RNA processing factors with their substrates. Component of the cytoplasmic LSM1-LSM7 complex, which is thought to be involved in mRNA degradation by activating the decapping step in the 5'-to-3' mRNA decay pathway. Component of the nucle...
Gene Name:
LSM6
Uniprot ID:
P62312
Uniprot Name:
U6 snRNA-associated Sm-like protein LSm6
Molecular Weight:
9127.525 Da
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:17139284 ]
  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:17016423 ]
  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:10592235 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Nucleoside-specific channel forming porin activity
Specific Function:
Constitutes the receptor for colicin K and phage T6, and functions as substrate-specific channel for nucleosides and deoxynucleosides.
Gene Name:
tsx
Uniprot ID:
P0A927
Uniprot Name:
Nucleoside-specific channel-forming protein tsx
Molecular Weight:
33588.835 Da
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:17139284 ]
  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:17016423 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nucleoside transmembrane transporter activity
Specific Function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs).
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Uniprot Name:
Equilibrative nucleoside transporter 1
Molecular Weight:
50218.805 Da
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:16818276 ]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 10:56