Thymine (BioCAD00000018554)

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Metabolite Card

Formula: C5H6N2O2 (126.0429)
SMILES: CC1=CNC(=O)NC1=O

Synonyms [en]

thymine; 5-methyluracil; 5-methyl-2,4(1H,3H)-pyrimidinedione; Thymin; Thy; 2,4-Dihydroxy-5-methylpyrimidine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Thymine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000018554). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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 was first isolated in 1893 by Albrecht Kossel and Albert Neumann from calves' thymus glands, hence its name. Thymine is one of the 4 nuelcoebases found in DNA and is essential to all life. Thymine exists in all living species, ranging from bacteria to plants to humans. Thymine combined with deoxyribose creates the nucleoside deoxythymidine (also called thymidine) which when phosphorylated to dTDP can be incorporated into DNA via DNA polymerases. Thymidine can be phosphorylated with up to three phosphoric acid groups, producing dTMP (deoxythymidine monophosphate) dTDP and/or dTTP. 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. Within humans, thymine participates in a number of enzymatic reactions. In particular, thymine and deoxyribose 1-phosphate can be biosynthesized from thymidine through its interaction with the enzyme thymidine phosphorylase. In addition, thymine can be converted into dihydrothymine; which is mediated by the enzyme dihydropyrimidine dehydrogenase [NADP(+)].

Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 123430-67-1
  • CAS Registry Number: 153445-43-3
  • CAS Registry Number: 2792-47-4
  • CAS Registry Number: 3059-73-2
  • CAS Registry Number: 3445-52-1
  • CAS Registry Number: 65-71-4
  • CAS Registry Number: 691841-57-3
  • CAS Registry Number: 69497-78-5
  • PubChem: 1135
  • PubChem: 3478
  • ChEBI: ChEBI:17821
  • HMDB: HMDB0000262
  • KEGG: C00178
  • BioCyc: THYMINE
  • NCBI MeSH: Thymine
  • Wikipedia: Thymine
  • DrugBank: DB03462
  • RefMet: RM0040235
  • MoNA: BAF_UVA_POS001013
  • MoNA: BAF_UVA_POS001014
  • MoNA: BAF_UVA_POS001015
  • MoNA: BAF_UVA_POS001016
  • MoNA: CCMSLIB00005720340
  • MoNA: EMBL_MCF_2_0_HRMS_Library000091
  • MoNA: EMBL_MCF_2_0_HRMS_Library000351
  • MoNA: FiehnLib001055
  • MoNA: HMDB0000262_c_ms_1108
  • MoNA: HMDB0000262_ms_ms_454
  • MoNA: HMDB0000262_ms_ms_455
  • MoNA: HMDB0000262_ms_ms_456
  • MoNA: JP009500
  • MoNA: KO001886
  • MoNA: KO001887
  • MoNA: KO001888
  • MoNA: KO001889
  • MoNA: KO001890
  • MoNA: KO004097
  • MoNA: KO004098
  • MoNA: KO004099
  • MoNA: KO004100
  • MoNA: KO004101
  • MoNA: KZ000077
  • MoNA: MoNA002229
  • MoNA: MoNA002230
  • MoNA: MoNA002231
  • MoNA: MoNA010143
  • MoNA: MoNA010144
  • MoNA: MoNA010145
  • MoNA: MoNA010146
  • MoNA: MoNA010147
  • MoNA: MoNA010148
  • MoNA: MoNA011375
  • MoNA: MoNA011376
  • MoNA: MoNA011377
  • MoNA: MoNA011378
  • MoNA: MoNA016804
  • MoNA: MoNA024315
  • MoNA: MoNA024358
  • MoNA: MoNA032521
  • MoNA: MoNA032522
  • MoNA: MoNA032523
  • MoNA: MoNA034629
  • MoNA: MoNA034630
  • MoNA: MoNA034631
  • MoNA: MoNA037336
  • MoNA: MoNA038083
  • MoNA: OUF00472
  • MoNA: PR010239
  • MoNA: PR100206
  • MoNA: PR100207
  • MoNA: PR100612
  • MoNA: PS036101
  • MoNA: PS036102
  • MoNA: PS036107
  • MoNA: PT103610
  • MoNA: PT103613
  • MoNA: PT203610
  • Metlin: METLIN_290
  • Coconut NaturalProduct: CNP0051852.0
  • Coconut NaturalProduct: CNP0143365.0
  • Coconut NaturalProduct: CNP0222722.0
  • Coconut NaturalProduct: CNP0517257.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01411 3.5.4.1 5-methylcytosine aminohydrolase
KEGG:R01412 1.14.11.6 thymine,2-oxoglutarate:oxygen oxidoreductase (7-hydroxylating)
KEGG:R01413 1.17.99.4 thymine:acceptor oxidoreductase
KEGG:R01414 1.3.1.1 5,6-dihydrothymine:NAD+ oxidoreductase
KEGG:R01415 1.3.1.2 5,6-dihydrothymine:NADP+ oxidoreductase
KEGG:R01570 2.4.2.2 thymidine:phosphate deoxy-alpha-D-ribosyltransferase
KEGG:R02806 2.4.2.6 nucleoside:purine(pyrimidine) deoxy-D-ribosyltransferase
KEGG:R09937 1.14.99.46 thymine,FMNH2:oxygen oxidoreductase (thymine hydroxylating, ring-opening)
KEGG:R11026 1.3.1.1 (R)-5,6-dihydrothymine:NAD+ oxidoreductase
KEGG:R12546 1.14.99.46 thymine,FMNH2:oxygen oxidoreductase (thymine hydroxylating, ring-opening)
KEGG:R12547 1.14.99.46 C00178 + C22379<=>C20256 + C22238
KEGG:R12956 3.2.2.10 thymidine 5'-monophosphate phosphodeoxyribohydrolase
BioCyc:THYM-PHOSPH-RXN 2.4.2.2 Pi + THYMIDINE<=>DEOXY-D-RIBOSE-1-PHOSPHATE + THYMINE
BioCyc:TRANS-RXN-362 thymine:proton symport
BioCyc:RXN-12886 1.14.99.46 THYMINE + OXYGEN-MOLECULE + FMNH2 + NADH --> CPD-22331 + WATER + FMN + NAD + PROTON
BioCyc:RXN-20708 THYMINE + CPD-24463 --> CPD-22331 + CPD-22329
BioCyc:RXN0-6565 1.3.1.1 DIHYDRO-THYMINE + NAD<=>THYMINE + NADH + PROTON
BioCyc:TRANS-RXN0-524 THYMINE --> THYMINE
BioCyc:RXN0-6468 CPLX0-11745 + THYMINE<=>CPLX0-8058
Rhea:RHEA:10317 1.14.11.6 thymine + 2-oxoglutarate + O2 => 5-hydroxymethyluracil + succinate + CO2
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Organism Source

Taxonomy Source

  1. Crocus sativus [ncbi taxid: 82528]
  2. Echinoclathria gibbosa [ncbi taxid: ]
  3. Equisetum hiemale [ncbi taxid: ]
  4. Escherichia coli [ncbi taxid: 562]
  5. FOOD SAKE [ncbi taxid: ]
  6. Junceella juncea [ncbi taxid: 252316]
  7. Phakellia mauritiana [ncbi taxid: ]
  8. Pinellia pedatisecta [ncbi taxid: 199222]
  9. Portulaca oleracea [ncbi taxid: 46147]
  10. Streptomyces piomogenus [ncbi taxid: 285508]
  11. Subergorgia suberosa [ncbi taxid: 767284]
  12. Viscum coloratum [ncbi taxid: 159976]
  13. Allium tuberosum [ncbi taxid: 4683]
  14. Aloe africana [ncbi taxid: 1080010]
  15. Aloe ferox [ncbi taxid: 117798]
  16. Aloe spicata [ncbi taxid: 992642]
  17. Aloe vera [ncbi taxid: 34199]
  18. Carthamus tinctorius [ncbi taxid: 4222]
  19. Cordyceps sinensis [ncbi taxid: ]
  20. Crinum asiaticum [ncbi taxid: 205937]
  21. Crocus sativus [ncbi taxid: 82528]
  22. Equisetum hiemale [ncbi taxid: ]
  23. Equisetum hyemale [ncbi taxid: 3262]
  24. Escherichia coli [ncbi taxid: 562]
  25. Euryale ferox [ncbi taxid: 4414]
  26. Fritillaria cirrhosa [ncbi taxid: 108544]
  27. Fritillaria delavayi [ncbi taxid: 152088]
  28. Fritillaria prezewalskii [ncbi taxid: ]
  29. Fritillaria przewalskii [ncbi taxid: 152092]
  30. Fritillaria taipaiensis [ncbi taxid: 152093]
  31. Fritillaria unibracteata [ncbi taxid: 152095]
  32. Fritillaria verticillata [ncbi taxid: 1352234]
  33. Ganoderma lucidum [ncbi taxid: 5315]
  34. Ganoderma sinense [ncbi taxid: 36075]
  35. Gastrodia elata [ncbi taxid: 91201]
  36. Ginkgo biloba [ncbi taxid: 3311]
  37. Homo sapiens [ncbi taxid: 9606]
  38. Liriope muscari [ncbi taxid: 39529]
  39. Lonicera japonica [ncbi taxid: 105884]
  40. Mus musculus [ncbi taxid: 10090]
  41. Ophiocordyceps sinensis [ncbi taxid: 72228]
  42. Ophiopogon japonicus [ncbi taxid: 100506]
  43. Pinellia pedatisecta [ncbi taxid: 199222]
  44. Stigma croci [ncbi taxid: ]
  45. Typha angustifolia [ncbi taxid: 59011]
  46. Typha orientalis [ncbi taxid: 644748]
  47. Xanthium strumarium [ncbi taxid: 318068]
  48. Ziziphus jujuba [ncbi taxid: 326968]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY-6430 thymine degradation
BioCyc:META_PWY-7181 pyrimidine deoxyribonucleosides degradation
BioCyc:META_PWY-6430 thymine degradation
BioCyc:ECO_PWY-7181 pyrimidine deoxyribonucleosides degradation
BioCyc:ECO_PWY0-181 salvage pathways of pyrimidine deoxyribonucleotides
BioCyc:ARA_PWY-6430 thymine degradation
BioCyc:TRYPANO_P1-PWY purine and pyrimidine metabolism
BioCyc:SHIGELLA_PWY0-1298 superpathway of pyrimidine deoxyribonucleosides degradation
BioCyc:PLASMO_P1-PWY purine and pyrimidine metabolism
BioCyc:MTBH37RV_PWY-7181 pyrimidine deoxyribonucleosides degradation
BioCyc:MTBCDC1551_PWY0-1298 superpathway of pyrimidine deoxyribonucleosides degradation
BioCyc:ECOO157_PWY0-1298 superpathway of pyrimidine deoxyribonucleosides degradation
BioCyc:ANTHRA_PWY0-1298 superpathway of pyrimidine deoxyribonucleosides degradation
BioCyc:ANTHRA_PWY-7181 pyrimidine deoxyribonucleosides degradation
BioCyc:AGRO_PWY0-1298 superpathway of pyrimidine deoxyribonucleosides degradation
BioCyc:AURANTIMONAS_PWY0-1298 superpathway of pyrimidine deoxyribonucleosides degradation
BioCyc:MOUSE_DRIBOPMET-PWY (deoxy)ribose phosphate degradation
BioCyc:SMAN_PWY0-181 salvage pathways of pyrimidine deoxyribonucleotides
BioCyc:SCO_P1-PWY salvage pathways of purine and pyrimidine nucleotides
BioCyc:SCO_DRIBOPMET-PWY (deoxy)ribose phosphate degradation
View All Pathways