Record Information |
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Version | 1.0 |
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Created at | 2020-04-17 18:41:34 UTC |
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Updated at | 2020-12-07 19:11:03 UTC |
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CannabisDB ID | CDB004834 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Thymidine |
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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 an extremely weak basic (essentially neutral) compound (based on its pKa). Thymidine exists in all living species, ranging from bacteria to humans. In cell biology it is used to synchronize the cells in S phase. Within humans, thymidine participates in a number of enzymatic reactions. 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 humans, thymidine is involved in the metabolic disorder called ump synthase deficiency (orotic aciduria). Outside of the human body, Thymidine has been detected, but not quantified in, several different foods, such as horned melons, asian pears, brassicas, japanese chestnuts, and apricots. This could make thymidine a potential biomarker for the consumption of these foods. Thymidine is a potentially toxic compound. Thymidine is non-toxic and is a naturally occurring compound that exists in all living organisms and DNA viruses. RNA does not have thymidine and has uridine instead. Thymidine is the DNA base T, which pairs with adenosine in double stranded DNA. 25% of DNA is composed of thymidine. Thymidine is a chemical compound which is a pyrimidine nucleoside. Thymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. Thymidine is a pyrimidine deoxynucleoside. Thymidine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C10H14N2O5 |
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Average Molecular Weight | 242.23 |
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Monoisotopic Molecular Weight | 242.0903 |
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IUPAC Name | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | thymidine |
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CAS Registry Number | 50-89-5 |
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SMILES | CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O |
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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 |
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InChI Key | IQFYYKKMVGJFEH-XLPZGREQSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Pyrimidine 2'-deoxyribonucleosides |
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Direct Parent | Pyrimidine 2'-deoxyribonucleosides |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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) |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-01dj-9300000000-6e24b5b6d36e07dd73d0 | 2018-05-25 | View Spectrum | GC-MS | Thymidine, 2 TMS, GC-MS Spectrum | splash10-0udi-1900000000-8e769118bc877facb05f | Spectrum | GC-MS | Thymidine, 3 TMS, GC-MS Spectrum | splash10-0ue9-2910000000-823bcee487948a9c786f | Spectrum | GC-MS | Thymidine, non-derivatized, GC-MS Spectrum | splash10-0udi-1900000000-8e769118bc877facb05f | Spectrum | GC-MS | Thymidine, non-derivatized, GC-MS Spectrum | splash10-0ue9-2910000000-823bcee487948a9c786f | Spectrum | GC-MS | Thymidine, non-derivatized, GC-MS Spectrum | splash10-0udi-0900000000-996530d1ea081ac2a7c7 | Spectrum | GC-MS | Thymidine, non-derivatized, GC-MS Spectrum | splash10-0l6r-0900000000-4645a52830204c8ef5d0 | Spectrum | GC-MS | Thymidine, non-derivatized, GC-MS Spectrum | splash10-0zfr-0900000000-76b8a050c10b514ed50b | Spectrum | Predicted GC-MS | Thymidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-9530000000-627a60bbe3e0b90f58cb | Spectrum | Predicted GC-MS | Thymidine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0g4i-7905000000-7b0c67709e3a5f91841a | Spectrum | Predicted GC-MS | Thymidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Thymidine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0900000000-1c2ba2f2aace4a76cdea | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-3900000000-d177672ef3f383adbb5d | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-01p9-9000000000-4483af567feecb34a651 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-0090000000-435be9f03e969dbabb79 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0006-5690000000-79b230d52929aa67bbf2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0006-9100000000-28a604508965067c85c5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-360e0667ff3d7d77e706 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-b1fecd2d1fa166e22d5f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-004i-1920000000-1a2e609b8a19ef491964 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-004i-1900000000-5e4a733641fa285e7f74 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-004i-3900000000-f734d5813fecb7a31814 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-01t9-5900000000-53b0016c66aa014c2abc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-03e9-9600000000-48f1a0d5512651a93e14 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-004i-1910000000-f02c2133ea475f4f838c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-08i0-2900000000-ec21970768da0fbf8ce5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-0002-9000000000-17c234cb0e8de5ae82f4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-014i-9000000000-d7e5ed251a93758682ec | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0090000000-435be9f03e969dbabb79 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-5690000000-79b230d52929aa67bbf2 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-9ad72ff6cb2e2dfab911 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-4900000000-3b1e6c50c2450e123648 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-6900000000-d30b05dfe1b6d25ebd2b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-052g-1940000000-ce16baa1ceb8a83565c2 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ufr-3920000000-c6ff3f238b6fed007635 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-104a4f5a4fe8a0ed5ca3 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Pyrimidine Metabolism | | | Beta Ureidopropionase Deficiency | | Not Available | UMP Synthase Deficiency (Orotic Aciduria) | | Not Available | Dihydropyrimidinase Deficiency | | Not Available | MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000273 |
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DrugBank ID | DB04485 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB031201 |
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KNApSAcK ID | C00019698 |
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Chemspider ID | 5585 |
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KEGG Compound ID | C00214 |
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BioCyc ID | THYMIDINE |
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BiGG ID | 50348 |
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Wikipedia Link | Thymidine |
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METLIN ID | 3375 |
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PubChem Compound | 5789 |
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PDB ID | Not Available |
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ChEBI ID | 17748 |
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References |
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General References | Not Available |
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