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Identification
Name2'-Deoxyuridine
Accession NumberDB02256  (EXPT01300)
Typesmall molecule
Groupsexperimental
Description

2'-Deoxyuridine. An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number951-78-0
WeightAverage: 228.202
Monoisotopic: 228.074621504
Chemical FormulaC9H12N2O5
InChI KeyMXHRCPNRJAMMIM-BBVRLYRLSA-N
InChI
InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8-/m0/s1
IUPAC Name
1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
OC[C@H]1O[C@@H](C[C@@H]1O)N1C=CC(=O)NC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassGlycosyl Compounds
Direct parentPyrimidine 2'-deoxyribonucleosides and Analogues
Alternative parentsPentoses; Pyrimidones; Hydropyrimidines; Tetrahydrofurans; Oxolanes; Secondary Alcohols; Polyamines; Primary Alcohols; Ethers
Substituentspentose monosaccharide; pyrimidone; pyrimidine; hydropyrimidine; monosaccharide; oxolane; tetrahydrofuran; secondary alcohol; ether; primary alcohol; polyamine; alcohol; organonitrogen compound; amine
Classification descriptionThis compound belongs to the pyrimidine 2'-deoxyribonucleosides and analogues. These are compounds consisting of a pyrimidine linked to a ribose which lacks an hydroxyl group at position 2.
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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9512
Blood Brain Barrier + 0.7655
Caco-2 permeable - 0.8937
P-glycoprotein substrate Non-substrate 0.7208
P-glycoprotein inhibitor I Non-inhibitor 0.8877
P-glycoprotein inhibitor II Non-inhibitor 0.8561
Renal organic cation transporter Non-inhibitor 0.8954
CYP450 2C9 substrate Non-substrate 0.7602
CYP450 2D6 substrate Non-substrate 0.8792
CYP450 3A4 substrate Non-substrate 0.5493
CYP450 1A2 substrate Non-inhibitor 0.9479
CYP450 2C9 substrate Non-inhibitor 0.9459
CYP450 2D6 substrate Non-inhibitor 0.9491
CYP450 2C19 substrate Non-inhibitor 0.9499
CYP450 3A4 substrate Non-inhibitor 0.9249
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.949
Ames test Non AMES toxic 0.8635
Carcinogenicity Non-carcinogens 0.8101
Biodegradation Ready biodegradable 0.5723
Rat acute toxicity 1.8101 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9411
hERG inhibition (predictor II) Non-inhibitor 0.8765
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point163 °CPhysProp
logP-1.51BALZARINI,JM ET AL. (1989)
Predicted Properties
PropertyValueSource
water solubility9.06e+01 g/lALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS-0.4ALOGPS
pKa (strongest acidic)9.71ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area99.1ChemAxon
rotatable bond count2ChemAxon
refractivity51.05ChemAxon
polarizability21.16ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Kenzo Watanabe, Yoshinori Kato, Masahiko Saito, Takeo Oba, Hisashi Fukushima, Takeshi Hara, “5-fluoro-2’-deoxyuridine derivatives and a process for the preparation thereof.” U.S. Patent US4605645, issued May, 1984.

US4605645
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00526
PubChem Compound1263358
PubChem Substance46506680
ChEBI16450
ChEMBL
HETDUR
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Uridine phosphorylase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Uridine phosphorylase P12758 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

2. Thymidylate synthase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Thymidylate synthase P0A884 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

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