Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2018-04-16 17:02:02 UTC |
---|
HMDB ID | HMDB0000262 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Thymine |
---|
Description | One of the pyrimidine bases of living matter. Derivation: Hydrolysis of deoxyribonucleic acid, from methylcyanoacetylurea by catalytic reduction. Use: Biochemical research. (Hawley's Condensed Chemical Dictionary). Thymine is a pyrimidine nucleobase. As the name implies, thymine may be derived by methylation of uracil at the 5th carbon. Thymine is found in the nucleic acid DNA. In RNA thymine is replaced with uracil in most cases. In DNA, thymine binds to adenine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
2,4-Dihydroxy-5-methylpyrimidine | ChEBI | 5-Methyl-2,4(1H,3H)-pyrimidinedione | ChEBI | 5-Methylpyrimidine-2,4(1H,3H)-dione | ChEBI | 5-Methyluracil | ChEBI | T | ChEBI | Thy | ChEBI | Thymin | ChEBI | 4-Hydroxy-5-methylpyrimidin-2(1H)-one | HMDB | 5-Methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione | HMDB | 5-Methyl-2,4-dihydroxypyrimidine | HMDB | 5-Methylpyrimidine-2,4-dione | HMDB | 5 Methyluracil | MeSH |
|
---|
Chemical Formula | C5H6N2O2 |
---|
Average Molecular Weight | 126.1133 |
---|
Monoisotopic Molecular Weight | 126.042927446 |
---|
IUPAC Name | 5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione |
---|
Traditional Name | thymine |
---|
CAS Registry Number | 65-71-4 |
---|
SMILES | CC1=CNC(=O)NC1=O |
---|
InChI Identifier | InChI=1S/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9) |
---|
InChI Key | RWQNBRDOKXIBIV-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | This compound belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Diazines |
---|
Sub Class | Pyrimidines and pyrimidine derivatives |
---|
Direct Parent | Hydroxypyrimidines |
---|
Alternative Parents | |
---|
Substituents | - Hydroxypyrimidine
- Heteroaromatic compound
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Biological role: Industrial application: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 320 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 3.82 mg/mL | YALKOWSKY,SH & DANNENFELSER,RM (1992) | LogP | -0.62 | HANSCH,C ET AL. (1995) |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0bt9-0960000000-50722d1f64f22b69e207 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0bta-0940000000-ff59d40c1a93e04954ab | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-05fr-7940000000-a0ebb190eba32aceac56 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0ab9-1980000000-5b95ad97f31d8176a0c6 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9500000000-74b6d7909610070d30d0 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0bt9-0960000000-50722d1f64f22b69e207 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0bta-0940000000-ff59d40c1a93e04954ab | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-05fr-7940000000-a0ebb190eba32aceac56 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0ab9-1980000000-5b95ad97f31d8176a0c6 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0bta-0930000000-a2d3bc738d3f9e60aeb7 | View in MoNA |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-9500000000-33bb743c9a1a77fe4e47 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0900000000-a3779faac812139c6333 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-0900000000-a3779faac812139c6333 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0udi-9200000000-0e7d9466530de47896d9 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-004i-9400000000-7ff00d5a94e12e6e1701 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-9100000000-1e96fdb2525aace8b29d | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0a6r-9000000000-34edf89b8a99493ed897 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9000000000-7d381bc0d559ed8150e9 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9000000000-90f8edce6ae2b6f83347 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4l-9000000000-445d07aed275008cfe2d | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-056r-8900000000-96370e30b48d3270abaa | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0bwc-9600000000-b988fb9252c409b19c33 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-01q9-9100000000-8c82d68e9ec8594b1fff | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-001i-9000000000-f69c5d963b845f8b3cfb | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0a4i-0900000000-3a9af2cf67d3f113fa7f | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-004i-0900000000-97549ff58b84351d860c | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-01q9-7900000000-5804e303580e1273f1a2 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-0900000000-deb5e6830bc01a0c870e | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9100000000-1e96fdb2525aace8b29d | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a6r-9000000000-34edf89b8a99493ed897 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-1900000000-7f378c898bdb1944116e | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-057i-9400000000-df8e4d4b901c8d1334fc | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfr-9000000000-629132689aa512d344b2 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-878180774da717dee4ae | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-005c-9400000000-2bf425b661913858b12a | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-87ca2758dbf67661c671 | View in MoNA |
---|
MS | Mass Spectrum (Electron Ionization) | splash10-056r-9400000000-5dd0bc0194a302d8ee95 | View in MoNA |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
---|
|
---|
General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
- Hofmann U, Schwab M, Seefried S, Marx C, Zanger UM, Eichelbaum M, Murdter TE: Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):371-80. [PubMed:12798197 ]
- van Lenthe H, van Kuilenburg AB, Ito T, Bootsma AH, van Cruchten A, Wada Y, van Gennip AH: Defects in pyrimidine degradation identified by HPLC-electrospray tandem mass spectrometry of urine specimens or urine-soaked filter paper strips. Clin Chem. 2000 Dec;46(12):1916-22. [PubMed:11106323 ]
- Allgayer H, Kolb M, Stuber V, Kruis W: Effects of bile acids on base hydroxylation in a model of human colonic mucosal DNA. Cancer Detect Prev. 2002;26(1):85-9. [PubMed:12088208 ]
- Goukassian D, Gad F, Yaar M, Eller MS, Nehal US, Gilchrest BA: Mechanisms and implications of the age-associated decrease in DNA repair capacity. FASEB J. 2000 Jul;14(10):1325-34. [PubMed:10877825 ]
- Wassberg C, Backvall H, Diffey B, Ponten F, Berne B: Enhanced epidermal ultraviolet responses in chronically sun-exposed skin are dependent on previous sun exposure. Acta Derm Venereol. 2003;83(4):254-61. [PubMed:12926795 ]
- Schilsky RL, O'Laughlin K, Ratain MJ: Phase I clinical and pharmacological study of thymidine (NSC 21548) and cis-diamminedichloroplatinum(II) in patients with advanced cancer. Cancer Res. 1986 Aug;46(8):4184-8. [PubMed:3731086 ]
- Maskell R, Okubadejo OA, Payne RH, Pead L: Human infections with thymine-requiring bacteria. J Med Microbiol. 1978 Feb;11(1):33-45. [PubMed:621731 ]
- Ling G, Chadwick CA, Berne B, Potten CS, Ponten J, Ponten F: Epidermal p53 response and repair of thymine dimers in human skin after a single dose of ultraviolet radiation: effects of photoprotection. Acta Derm Venereol. 2001 May;81(2):81-6. [PubMed:11501666 ]
- Young AR, Sheehan JM, Chadwick CA, Potten CS: Protection by ultraviolet A and B sunscreens against in situ dipyrimidine photolesions in human epidermis is comparable to protection against sunburn. J Invest Dermatol. 2000 Jul;115(1):37-41. [PubMed:10886505 ]
- Maskell R, Okubadejo OA, Payne RH: Thymine-requiring bacteria associated with co-trimoxazole therapy. Lancet. 1976 Apr 17;1(7964):834-5. [PubMed:56651 ]
- Courdavault S, Baudouin C, Sauvaigo S, Mouret S, Candeias S, Charveron M, Favier A, Cadet J, Douki T: Unrepaired cyclobutane pyrimidine dimers do not prevent proliferation of UV-B-irradiated cultured human fibroblasts. Photochem Photobiol. 2004 Feb;79(2):145-51. [PubMed:15068027 ]
- Alsarra IA, Alarifi MN: Validated liquid chromatographic determination of 5-fluorouracil in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 May 25;804(2):435-9. [PubMed:15081940 ]
- Castro-Gago M, Camina F, Lojo S, Rodriguez-Segade S, Rodriguez-Nunez A: Concentrations of purine nucleotides and purine and pyrimidine bases in cerebrospinal fluid of neurologically healthy children. Eur J Clin Chem Clin Biochem. 1992 Nov;30(11):761-5. [PubMed:1489848 ]
- Placzek M, Gaube S, Kerkmann U, Gilbertz KP, Herzinger T, Haen E, Przybilla B: Ultraviolet B-induced DNA damage in human epidermis is modified by the antioxidants ascorbic acid and D-alpha-tocopherol. J Invest Dermatol. 2005 Feb;124(2):304-7. [PubMed:15675947 ]
- Thienpont LM, Van Landuyt KG, Stockl D, Saeyens W, De Keukeleire D, De Leenheer AP: Evaluation of 2-iminoimidazolidin-4-one and thymine as respective internal standards for normal-phase and reversed-phase high-performance liquid chromatographic determination of creatinine in human serum. J Chromatogr B Biomed Appl. 1995 Mar 10;665(1):63-9. [PubMed:7795802 ]
- Rodriguez Ortner E, Hayes RB, Weissfeld J, Gelmann EP: Effect of homeodomain protein NKX3.1 R52C polymorphism on prostate gland size. Urology. 2006 Feb;67(2):311-5. Epub 2006 Jan 25. [PubMed:16442598 ]
- Antille C, Tran C, Sorg O, Carraux P, Didierjean L, Saurat JH: Vitamin A exerts a photoprotective action in skin by absorbing ultraviolet B radiation. J Invest Dermatol. 2003 Nov;121(5):1163-7. [PubMed:14708621 ]
|
---|