Identification

Name
Uridine
Accession Number
DB02745  (EXPT03205)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
WHI7HQ7H85
CAS number
58-96-8
Weight
Average: 244.2014
Monoisotopic: 244.069536126
Chemical Formula
C9H12N2O6
InChI Key
DRTQHJPVMGBUCF-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UU6 snRNA-associated Sm-like protein LSm6Not AvailableHuman
UNucleoside-specific channel-forming protein tsxNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Beta Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00296
KEGG Compound
C00299
PubChem Compound
6029
PubChem Substance
46507015
ChemSpider
5807
ChEBI
16704
ChEMBL
CHEMBL100259
Therapeutic Targets Database
DNC001491
PharmGKB
PA130230921
HET
URI
Wikipedia
Uridine
PDB Entries
1i5l / 1lnx / 1loj / 1tlz / 2fr6 / 2hwu / 2v0l / 3ivd / 3tij / 4eg2
show 17 more

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

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00kb-1970000000-d1bfa838a4e9fa77c862
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00kb-1960000000-a8283468b762a8520102
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-1950000000-70fdf4785544d0968f70
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-9520000000-591c0bcf8f956d710367
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-066s-2970000000-36fbef6f6b10c2895df4
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-1890000000-dd0569d4351a64c566c9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kb-1970000000-d1bfa838a4e9fa77c862
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kb-1960000000-a8283468b762a8520102
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1950000000-70fdf4785544d0968f70
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9520000000-591c0bcf8f956d710367
GC-MS Spectrum - GC-MSGC-MSsplash10-066s-2970000000-36fbef6f6b10c2895df4
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1890000000-dd0569d4351a64c566c9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014j-1940000000-8b7a5ce66afa9b9bf939
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00kb-1950000000-00519445de22f955367d
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-03di-0900000000-7010b37007f5c3d9ce1f
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-03di-3900000000-b4639c8c89eac6158da6
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-022a-9200000000-f8472930d09b32f54790
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0291000000-aebaa77a411473acb859
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014j-9000000000-205562662b564ebdca28
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-776595fd1c19f6ec51cd
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-10358e53c56bcb50ed4c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0971000000-f989283d2dec564a3af0
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00kf-9000000000-c11e7bfdec0b5c7bf450
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-9000000000-104e62fbffc4110779ef
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-eaf6ff9ac3971d6f045f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-052f-0697120000-c9fd5b8d641165d84e92
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-9000000000-995de18be458c48a8d2d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0590000000-4d1d6aba25697dd11da8
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0uki-0190000000-3aea11527d0520158d77
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004l-0291010000-c8f22405e9290fccc011
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0490000000-1a2f990a874bb1868249
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0090000000-c8efbe58f0df63698b2c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0090000000-7495d9b948a8e3b7b83b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03dj-3960000000-3466ccfdf88139ddf140
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-03di-3900000000-0d08e4a7d4b8aacee6e6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-03di-4900000000-d942ee27b3ca1d6ef94d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-03di-9700000000-594c7bb6dc6de848ff11
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-022d-9100000000-2826c4eb794745ec3148
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-03di-0910000000-617b4ec6cf749942c0cd
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-03di-5900000000-69944d9ce81849ec71c6
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0ikc-2970000000-089539e61aec5eeed279
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0w2c-0970000000-e6a764f50c4a9c460396
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0udi-0690000000-357cb54739a10dfcbd65
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-9000000000-995de18be458c48a8d2d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0590000000-4d1d6aba25697dd11da8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0uki-0190000000-3aea11527d0520158d77
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0490000000-1a2f990a874bb1868249
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-d9e34a80f1a6b4481494
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0090000000-7495d9b948a8e3b7b83b
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0ikc-2970000000-089539e61aec5eeed279
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03dj-3960000000-3466ccfdf88139ddf140
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-3900000000-305d7746674473d0fdf5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-4900000000-10340fb76655d3f993a0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-9700000000-1ddefb0b972a63b62682
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-022d-9100000000-2826c4eb794745ec3148
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03di-0910000000-566ed331b13b3c9cf8e9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-9000000000-205562662b564ebdca28
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-776595fd1c19f6ec51cd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-10358e53c56bcb50ed4c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kf-9000000000-c11e7bfdec0b5c7bf450
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-aa4ba481865df59b0da8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-eaf6ff9ac3971d6f045f
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Not Available
Direct Parent
Pyrimidine nucleosides
Alternative Parents
Glycosylamines / Pentoses / Pyrimidones / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Vinylogous amides / Ureas / Lactams / Secondary alcohols
show 7 more
Substituents
Pyrimidine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Pyrimidone / Hydropyrimidine / Monosaccharide / Pyrimidine / Vinylogous amide / Tetrahydrofuran
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
uridines (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 sub...
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...
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 November 09, 2017 03:18