<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:20 UTC</creation_date>
  <update_date>2019-11-26 03:07:32 UTC</update_date>
  <accession>FDB012757</accession>
  <name>Thymine 2-desoxyriboside</name>
  <description>Isolated from seedlings of Phaseolus vulgaris (kidney bean)

Deoxythymidine is non-toxic and as part of one of the four nucleotides in DNA it is a naturally occurring compound that exists in all living organisms and DNA viruses. RNA has uridine (uracil joined to ribose) instead. Uracil is chemically very similar to thymine, the latter being 5-methyluracil. Since thymine nucleotides are precursors of DNA, not RNA, the prefix "deoxy" is often left out, i.e., deoxythymidine is often just called thymidine.; In its composition, deoxythymidine is a nucleoside composed of deoxyribose (a pentose sugar) joined to the pyrimidine base thymine.; Iododeoxyuridine is a radiosensitizer and increases the amount of DNA damage received from ionizing radiation.; Thymidine (more precisely called deoxythymidine; can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound, more precisely 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.; Thymidine is non-toxic and is a naturally occurring compound that exists in all living organisms and DNA viruses. 25% of DNA is composed of thymidine. RNA does not have thymidine and has uridine instead. Thymidine is a chemical compound which is a pyrimidine nucleoside. Thymidine is the DNA base T, which pairs with adenosine in double stranded DNA. Thymine 2-desoxyriboside is found in pulses, yellow wax bean, and green bean.</description>
  <synonyms>
    <synonym>(3H)Thymidine</synonym>
    <synonym>&amp;beta;-D-Ribofuranoside, thymine-1 2-deoxy-</synonym>
    <synonym>1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione, 9CI</synonym>
    <synonym>1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-(2-Deoxy-b-D-ribofuranosyl)-5-methyluracil</synonym>
    <synonym>1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-(2-Deoxy-beta-D-ribofuranosyl)-5-methyluracil</synonym>
    <synonym>1-(2-Deoxy-beta-D-ribofuranosyl)thymine</synonym>
    <synonym>1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-beta-ribofuranosyl)-5-methyluracil</synonym>
    <synonym>1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione</synonym>
    <synonym>2-deoxythymidine</synonym>
    <synonym>2-Desoxy-thymidine</synonym>
    <synonym>2'-deoxy-5-methyl-Uridine</synonym>
    <synonym>2'-deoxy-5-methyluridine</synonym>
    <synonym>2'-Deoxythymidine</synonym>
    <synonym>2'-thymidine</synonym>
    <synonym>5-Methyl-2'-deoxyuridine</synonym>
    <synonym>5-Methyldeoxyuridine</synonym>
    <synonym>5-Methyldeoxyurindine</synonym>
    <synonym>beta-D-Ribofuranoside, thymine-1 2-deoxy-</synonym>
    <synonym>Deoxyribothymidine</synonym>
    <synonym>Deoxythymidin</synonym>
    <synonym>Deoxythymidine</synonym>
    <synonym>Desoxy-thymidin</synonym>
    <synonym>DT</synonym>
    <synonym>DTHD</synonym>
    <synonym>Dthyd</synonym>
    <synonym>NSC 21548</synonym>
    <synonym>THM</synonym>
    <synonym>Thymidin</synonym>
    <synonym>Thymidine</synonym>
    <synonym>Thymidine (8CI,9CI)</synonym>
    <synonym>Thymidine-(H-3)</synonym>
    <synonym>Thymidine, 2'-deoxy-</synonym>
    <synonym>Thymidine, labeled with tritium</synonym>
    <synonym>Thymine 2-desoxyriboside</synonym>
    <synonym>thymine 2'-deoxyriboside</synonym>
    <synonym>Thymine deoxyriboside</synonym>
    <synonym>thymine-1 2-deoxy-b-D-Ribofuranoside</synonym>
    <synonym>thymine-1 2-deoxy-beta-delta-Ribofuranoside</synonym>
    <synonym>Thymine-2-deoxyriboside</synonym>
    <synonym>Thymine-2-desoxyriboside</synonym>
    <synonym>Thyminedeoxyriboside</synonym>
    <synonym>Thymosine</synonym>
    <synonym>Tritiated thymidine</synonym>
    <synonym>Uridine, 2'-deoxy-5-methyl-</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O5</chemical_formula>
  <average_molecular_weight>242.2286</average_molecular_weight>
  <monisotopic_moleculate_weight>242.090271568</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxy-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>4-hydroxy-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one</traditional_iupac>
  <cas_registry_number>50-89-5</cas_registry_number>
  <smiles>CC1=CN(C2CC(O)C(CO)O2)C(=O)N=C1O</smiles>
  <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)</inchi>
  <inchikey>IQFYYKKMVGJFEH-UHFFFAOYSA-N</inchikey>
  <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.</description>
    <direct_parent>Pyrimidine 2'-deoxyribonucleosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class>Pyrimidine 2'-deoxyribonucleosides</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a deoxynucleoside</external_descriptor>
      <external_descriptor>a pyrimidine-related compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.98e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 186-187°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>7.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-hydroxy-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>242.2286</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>242.090271568</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1=CN(C2CC(O)C(CO)O2)C(=O)N=C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H14N2O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>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)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>IQFYYKKMVGJFEH-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>102.59</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>55.73</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>23.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP00046</smpdb_id>
      <kegg_map_id>map00240</kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>221276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>112542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>126052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>919942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441513</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00273</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>17748</chebi_id>
  <biocyc_id/>
  <het_id>THM</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce30d1a0c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d181d0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0fe68&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0fcb0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0faf8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0f940&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0f710&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0f490&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0f2b0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0f008&gt;</reference>
    <reference>#&lt;Reference:0x000055ce30d0ee50&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Beer</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Green bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pulses</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific></name_scientific>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Yellow wax bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Cytosolic 5'-nucleotidase 3</name>
      <uniprot_id>Q9H0P0</uniprot_id>
      <uniprot_name/>
      <gene_name>NT5C3</gene_name>
    </enzyme>
    <enzyme>
      <name>Thymidine kinase 2, mitochondrial</name>
      <uniprot_id>O00142</uniprot_id>
      <uniprot_name/>
      <gene_name>TK2</gene_name>
    </enzyme>
    <enzyme>
      <name>Thymidine kinase, cytosolic</name>
      <uniprot_id>P04183</uniprot_id>
      <uniprot_name/>
      <gene_name>TK1</gene_name>
    </enzyme>
    <enzyme>
      <name>Thymidine phosphorylase</name>
      <uniprot_id>P19971</uniprot_id>
      <uniprot_name/>
      <gene_name>TYMP</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
