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Record Information
Version1.0
Creation Date2016-09-30 22:27:43 UTC
Update Date2020-05-21 16:29:01 UTC
MCDB ID BMDB0000273
Secondary Accession Numbers
  • BMDB00273
Metabolite Identification
Common NameThymidine
DescriptionThymidine, also known as deoxythymidine or DTHD, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Thymidine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Thymidine exists in all living species, ranging from bacteria to humans. Thymidine participates in a number of enzymatic reactions, within cattle. In particular, Thymidine can be biosynthesized from 5-thymidylic acid through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In addition, Thymidine can be converted into 5-thymidylic acid; which is catalyzed by the enzyme thymidine kinase, cytosolic. In cattle, thymidine is involved in the metabolic pathway called the pyrimidine metabolism pathway. Thymidine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dioneChEBI
2'-Deoxy-5-methyluridineChEBI
2'-DeoxythymidineChEBI
2'-ThymidineChEBI
5-Methyl-2'-deoxyuridineChEBI
DeoxythymidineChEBI
DTHDChEBI
TChEBI
Thymine 2'-deoxyribosideChEBI
1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dioneGenerator
1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dioneGenerator
1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedioneHMDB
1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedioneHMDB
1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dioneHMDB
2'-Deoxy-5-methyl-uridineHMDB
5-MethyldeoxyuridineHMDB
DeoxyribothymidineHMDB
DTHMDB
DThydHMDB
ThymidinHMDB
Thymine 2-desoxyribosideHMDB
Thymine deoxyribosideHMDB
Thymine-1 2-deoxy-b-D-ribofuranosideHMDB
Thymine-1 2-deoxy-beta-delta-ribofuranosideHMDB
2' DeoxythymidineHMDB
Chemical FormulaC10H14N2O5
Average Molecular Weight242.2286
Monoisotopic Molecular Weight242.090271568
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number50-89-5
SMILESNot Available
InChI Identifier
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+/m0/s1
InChI KeyIQFYYKKMVGJFEH-XLPZGREQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Pyrimidone
  • Hydroxypyrimidine
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility73.5 mg/mLNot Available
LogP-0.93SANGSTER (1993)
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000273
DrugBank IDDB04485
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031201
KNApSAcK IDC00019698
Chemspider ID5585
KEGG Compound IDC00214
BioCyc IDTHYMIDINE
BiGG ID50348
Wikipedia LinkThymidine
METLIN ID3375
PubChem Compound5789
PDB IDNot Available
ChEBI ID17748
References
Synthesis ReferenceHerdewijn, P.; Kerremans, L.; Wigerinck, P.; Vandendriessche, F.; Van Aerschot, A. Synthesis of thymidine from 5-iodo-2'-deoxyuridine. Tetrahedron Letters (1991), 32(34), 4397-400.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]