You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDeoxythymidine
Accession NumberDB04485  (EXPT03053)
TypeSmall Molecule
GroupsExperimental
Description

Deoxythymidine is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase.

Structure
Thumb
Synonyms
SynonymLanguageCode
2'-DeoxythymidineNot AvailableNot Available
deoxyribosylthymineNot AvailableNot Available
ThymidineNot AvailableNot Available
thymine deoxyribosideNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number50-89-5
WeightAverage: 242.2286
Monoisotopic: 242.090271568
Chemical FormulaC10H14N2O5
InChI KeyIQFYYKKMVGJFEH-GJMOJQLCSA-N
InChI
InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8-/m1/s1
IUPAC Name
1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
CC1=CN([C@H]2C[C@@H](O)[C@H](CO)O2)C(=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
Pathways
PathwayCategorySMPDB ID
Beta Ureidopropionase DeficiencyDiseaseSMP00172
Pyrimidine MetabolismMetabolicSMP00046
Dihydropyrimidinase DeficiencyDiseaseSMP00178
UMP Synthase Deiciency (Orotic Aciduria)DiseaseSMP00219
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)DiseaseSMP00202
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.971
Blood Brain Barrier + 0.5902
Caco-2 permeable - 0.8851
P-glycoprotein substrate Non-substrate 0.6468
P-glycoprotein inhibitor I Non-inhibitor 0.8872
P-glycoprotein inhibitor II Non-inhibitor 0.9128
Renal organic cation transporter Non-inhibitor 0.9072
CYP450 2C9 substrate Non-substrate 0.6893
CYP450 2D6 substrate Non-substrate 0.8834
CYP450 3A4 substrate Non-substrate 0.5083
CYP450 1A2 substrate Non-inhibitor 0.9529
CYP450 2C9 substrate Non-inhibitor 0.9392
CYP450 2D6 substrate Non-inhibitor 0.9491
CYP450 2C19 substrate Non-inhibitor 0.9479
CYP450 3A4 substrate Non-inhibitor 0.9308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9415
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.7872
Biodegradation Not ready biodegradable 0.5131
Rat acute toxicity 1.8754 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9358
hERG inhibition (predictor II) Non-inhibitor 0.8734
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point186.5 °CPhysProp
logP-0.93SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility66.8ALOGPS
logP-1.3ALOGPS
logP-1.1ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.41 m3·mol-1ChemAxon
Polarizability23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Jeffrey D. Wilson, “Preparation of 3’azido-3-’-deoxythymidine.” U.S. Patent US4921950, issued October, 1986.

US4921950
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00214
PubChem Compound3000346
PubChem Substance46507598
BindingDB1
ChEBI17748
ChEMBL
HETTHM
WikipediaThymidine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Thymidine kinase

Kind: protein

Organism: EHV-4

Pharmacological action: unknown

Components

Name UniProt ID Details
Thymidine kinase P24425 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. Thymidine kinase 2, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Thymidine kinase 2, mitochondrial O00142 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

3. Glucose-1-phosphate thymidylyltransferase

Kind: protein

Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)

Pharmacological action: unknown

Components

Name UniProt ID Details
Glucose-1-phosphate thymidylyltransferase Q9HU22 Details

4. 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

5. Thymidylate kinase

Kind: protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
Thymidylate kinase O05891 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

6. Thymidine kinase

Kind: protein

Organism: HHV-1

Pharmacological action: unknown

Components

Name UniProt ID Details
Thymidine kinase P03176 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

7. 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

Transporters

1. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. Pubmed

2. Solute carrier family 28 member 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Solute carrier family 28 member 3 Q9HAS3 Details

References:

  1. Badagnani I, Chan W, Castro RA, Brett CM, Huang CC, Stryke D, Kawamoto M, Johns SJ, Ferrin TE, Carlson EJ, Burchard EG, Giacomini KM: Functional analysis of genetic variants in the human concentrative nucleoside transporter 3 (CNT3; SLC28A3). Pharmacogenomics J. 2005;5(3):157-65. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:24