| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:27:43 UTC |
|---|
| Update Date | 2020-05-21 16:29:01 UTC |
|---|
| BMDB ID | BMDB0000273 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Thymidine |
|---|
| Description | Thymidine, 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 | |
|---|
| Synonyms | | Value | Source |
|---|
| 1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione | ChEBI | | 2'-Deoxy-5-methyluridine | ChEBI | | 2'-Deoxythymidine | ChEBI | | 2'-Thymidine | ChEBI | | 5-Methyl-2'-deoxyuridine | ChEBI | | Deoxythymidine | ChEBI | | DTHD | ChEBI | | T | ChEBI | | Thymine 2'-deoxyriboside | ChEBI | | 1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione | Generator | | 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione | Generator | | 1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione | HMDB | | 1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione | HMDB | | 1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione | HMDB | | 2'-Deoxy-5-methyl-uridine | HMDB | | 5-Methyldeoxyuridine | HMDB | | Deoxyribothymidine | HMDB | | DT | HMDB | | DThyd | HMDB | | Thymidin | HMDB | | Thymine 2-desoxyriboside | HMDB | | Thymine deoxyriboside | HMDB | | Thymine-1 2-deoxy-b-D-ribofuranoside | HMDB | | Thymine-1 2-deoxy-beta-delta-ribofuranoside | HMDB | | 2' Deoxythymidine | HMDB |
|
|---|
| Chemical Formula | C10H14N2O5 |
|---|
| Average Molecular Weight | 242.2286 |
|---|
| Monoisotopic Molecular Weight | 242.090271568 |
|---|
| IUPAC Name | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione |
|---|
| Traditional Name | thymidine |
|---|
| CAS Registry Number | 50-89-5 |
|---|
| SMILES | CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O |
|---|
| 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 Key | IQFYYKKMVGJFEH-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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Nucleosides, nucleotides, and analogues |
|---|
| Class | Pyrimidine nucleosides |
|---|
| Sub Class | Pyrimidine 2'-deoxyribonucleosides |
|---|
| Direct Parent | Pyrimidine 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 Framework | Aromatic heteromonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected but not Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | - Cytoplasm
- Lysosome
- Mitochondria
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 73.5 mg/mL | Not Available | | LogP | -0.93 | SANGSTER (1993) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Synthesis Reference | Herdewijn, 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. |
|---|
| General References | - 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 ]
|
|---|
