Human Metabolome Database: Showing metabocard for Thymine (HMDB0000262)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2019-12-04 21:53:50 UTC

HMDB ID

HMDB0000262

Secondary Accession Numbers

HMDB00262

Metabolite Identification

Common Name

Thymine

Description

Thymine, also known as 5-methyluracil, 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. Thymine (T, Thy) is one of the four nucleobases in the nucleic acid of DNA that are represented by the letters G–C–A–T. Thymine is a drug. Thymine is an extremely weak basic (essentially neutral) compound (based on its pKa). Thymine was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calves' thymus glands, hence its name. Thymine exists in all living species, ranging from bacteria to humans. Within humans, thymine participates in a number of enzymatic reactions. In particular, thymine and deoxyribose 1-phosphate can be biosynthesized from thymidine; which is mediated by the enzyme thymidine phosphorylase. In addition, thymine can be converted into dihydrothymine through the action of the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In humans, thymine is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, thymine has been detected, but not quantified in, several different foods, such as mammee apples, nances, angelica, rocket salad (ssp.), and common chokecherries. This could make thymine a potential biomarker for the consumption of these foods. Thymine is a potentially toxic compound. Thymine has been found to be associated with several diseases such as temporomandibular joint disorder, colorectal cancer, and thymidine treatment; also thymine has been linked to several inborn metabolic disorders including dihydropyrimidine dehydrogenase deficiency and beta-ureidopropionase deficiency. In RNA, thymine is replaced with uracil in most cases. In March 2015, NASA scientists reported that, for the first time, complex DNA and RNA organic compounds of life, including uracil, cytosine and thymine, have been formed in the laboratory under outer space conditions, using starting chemicals, such as pyrimidine, found in meteorites. One of the common mutations of DNA involves two adjacent thymines or cytosine, which, in presence of ultraviolet light, may form thymine dimers, causing "kinks" in the DNA molecule that inhibit normal function. Thymine has not been found in meteorites, which suggests the first strands of DNA had to look elsewhere to obtain this building block.

Structure

MOL SDF PDB SMILES InChI

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	HMDB

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

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

pyrimidone (CHEBI:17821 )
pyrimidine nucleobase (CHEBI:17821 )
pyrimidines (C00178 )
a pyrimidine-related compound (THYMINE )
a pyrimidine base (THYMINE )

Ontology

Physiological effect

Health effect:

Observation:

Periodontal Probing Depth

Health condition:

Metabolism and nutrition disorders:

Dihydropyrimidine dehydrogenase deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Cell:

Fibroblast

Process

Naturally occurring process:

Metabolite

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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

Property	Value	Source
Water Solubility	10.8 g/L	ALOGPS
logP	-0.99	ALOGPS
logP	-0.46	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.33 m³·mol⁻¹	ChemAxon
Polarizability	11.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0bt9-0960000000-50722d1f64f22b69e207	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0bta-0940000000-ff59d40c1a93e04954ab	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-05fr-7940000000-a0ebb190eba32aceac56	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0ab9-1980000000-5b95ad97f31d8176a0c6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9500000000-74b6d7909610070d30d0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0bt9-0960000000-50722d1f64f22b69e207	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0bta-0940000000-ff59d40c1a93e04954ab	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-7940000000-a0ebb190eba32aceac56	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ab9-1980000000-5b95ad97f31d8176a0c6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0bta-0930000000-a2d3bc738d3f9e60aeb7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9500000000-33bb743c9a1a77fe4e47	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-a3779faac812139c6333	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0900000000-a3779faac812139c6333	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-9200000000-0e7d9466530de47896d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-004i-9400000000-7ff00d5a94e12e6e1701	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-9100000000-1e96fdb2525aace8b29d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a6r-9000000000-34edf89b8a99493ed897	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-7d381bc0d559ed8150e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-90f8edce6ae2b6f83347	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9000000000-445d07aed275008cfe2d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-056r-8900000000-96370e30b48d3270abaa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0bwc-9600000000-b988fb9252c409b19c33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-01q9-9100000000-8c82d68e9ec8594b1fff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-f69c5d963b845f8b3cfb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a4i-0900000000-3a9af2cf67d3f113fa7f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-97549ff58b84351d860c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-01q9-7900000000-5804e303580e1273f1a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-0900000000-deb5e6830bc01a0c870e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-1e96fdb2525aace8b29d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-9000000000-34edf89b8a99493ed897	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-7f378c898bdb1944116e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-057i-9400000000-df8e4d4b901c8d1334fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9000000000-629132689aa512d344b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-878180774da717dee4ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005c-9400000000-2bf425b661913858b12a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-87ca2758dbf67661c671	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9400000000-5dd0bc0194a302d8ee95	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Fibroblasts
Prostate
Skin

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Cerebrospinal Fluid (CSF)	Detected and Quantified	<5.0 uM	Adult (>18 years old)	Both	Normal	18502700	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 - 0.1 uM	Adult (>18 years old)	Both	Normal	15385443	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25670064	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified		Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	5.91 +/- 11.2 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.81 +/- 2.51 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	8.82 +/- 13.15 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	2.89 +/- 4.53 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	3.51 +/- 3.10 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.655 +/- 1.44 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.10 (0.045-0.16) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9857238	details
Urine	Detected and Quantified	0.16 (0.065-0.26) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9857238	details
Urine	Detected and Quantified	0-9 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0.202 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12798197	details
Urine	Detected and Quantified	0.791 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2109146	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1390.0 +/- 150.0 uM	Adult (>18 years old)	Both	Solid tumors	6736109	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.04 - 0.2 uM	Adult (>18 years old)	Not Specified	Beta-ureidopropionase deficiency	15385443	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected and Quantified	2.61 +/- 2.39 uM	Adult (>18 years old)	Both	Temporomandibular joint disorder (TMD)	Sugimoto et al. (...	details
Urine	Detected and Quantified	343.024 umol/mmol creatinine	Adult (>18 years old)	Female	Dihydropyrimidine dehydrogenase (DPD) deficiency	2109146	details
Urine	Detected and Quantified	468.0684 umol/mmol creatinine	Children (1 - 13 years old)	Male	Dihydropyrimidine dehydrogenase (DPD) deficiency	2109146	details

Associated Disorders and Diseases

Disease References

Thymidine treatment
Leyva A, Schornagel JH, Kraal I, Wadman SK, Pinedo HM: Clinical and biochemical studies of high-dose thymidine treatment in patients with solid tumors. J Cancer Res Clin Oncol. 1984;107(3):211-6. [PubMed:6736109 ]
Beta-ureidopropionase deficiency
van Kuilenburg AB, Meinsma R, Beke E, Assmann B, Ribes A, Lorente I, Busch R, Mayatepek E, Abeling NG, van Cruchten A, Stroomer AE, van Lenthe H, Zoetekouw L, Kulik W, Hoffmann GF, Voit T, Wevers RA, Rutsch F, van Gennip AH: beta-Ureidopropionase deficiency: an inborn error of pyrimidine degradation associated with neurological abnormalities. Hum Mol Genet. 2004 Nov 15;13(22):2793-801. Epub 2004 Sep 22. [PubMed:15385443 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Temporomandibular joint disorder
(). Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles. . .
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Dihydropyrimidine dehydrogenase deficiency
Brockstedt M, Jakobs C, Smit LM, van Gennip AH, Berger R: A new case of dihydropyrimidine dehydrogenase deficiency. J Inherit Metab Dis. 1990;13(1):121-4. [PubMed:2109146 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.

Associated OMIM IDs

613161 (Beta-ureidopropionase deficiency)
114500 (Colorectal cancer)
274270 (Dihydropyrimidine dehydrogenase deficiency)

External Links

DrugBank ID

DB03462

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17821

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Zhang, Shi-Ying; Wu, Da-Jun; Zhang, Yan-Ping. Synthesis of thymine. Zhongguo Yiyao Gongye Zazhi (1999), 30(7), 325.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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Enzymes

Enzyme Details

1. Dihydropyrimidine dehydrogenase [NADP(+)]

General function:: Involved in electron carrier activity
Specific function:: Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
Gene Name:: DPYD
Uniprot ID:: Q12882
Molecular weight:: 111400.32

Reactions

Dihydrothymine + NADP → Thymine + NADPH + Hydrogen Ion	details

Enzyme Details

2. Thymidine phosphorylase

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:: TYMP
Uniprot ID:: P19971
Molecular weight:: 49954.965

Reactions

Thymidine + Phosphate → Thymine + Deoxyribose 1-phosphate	details

Showing metabocard for Thymine (HMDB0000262)

Structure for HMDB0000262 (Thymine)

Enzymes

Reactions

Reactions