Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:50 UTC
HMDB IDHMDB01227
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Thymidylic acid
Description5-Thymidylic acid is a thymine nucleotide. Also known as thymidine monophosphate, and abbreviated TMP, is a nucleotide that is found in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. TMP consists of a phosphate group, esterified to the the pentose sugar deoxyribose moiety, and the nucleobase thymine. In mammalian cells, thymidine deprivation induces chromosome aberrations such as chromatid breaks, chromatid interchanges, and chromosome fragmentation. (PMID 3888175 ).
Structure
Thumb
Synonyms
  1. 2'-Deoxythymidine 5'-monophosphate
  2. 5'-dTMP
  3. 5'-Thymidylate
  4. 5'-Thymidylic acid
  5. 5'-TMP
  6. 5-Methyl-dUMP
  7. Deoxy TMP
  8. Deoxyribosylthymine monophosphate
  9. Deoxythymidine 5'-monophosphate
  10. Deoxythymidine 5'-phosphate
  11. Deoxythymidine monophosphate
  12. Deoxythymidylate
  13. Deoxythymidylic acid
  14. Deoxythymydilate
  15. Deoxythymydilic acid
  16. dTMP
  17. Thymidine 5'-monophosphate
  18. Thymidine 5'-phosphate
  19. Thymidine 5'-phosphorate
  20. Thymidine 5'-phosphoric acid
  21. Thymidine 5'MP
  22. Thymidine mononucleotide
  23. Thymidine monophosphate
  24. Thymidine phosphate
  25. Thymidine-5'-monophosphorate
  26. Thymidine-5'-monophosphoric acid
  27. Thymidylate
  28. Thymidylic acid
Chemical FormulaC10H15N2O8P
Average Molecular Weight322.2085
Monoisotopic Molecular Weight322.056601978
IUPAC Name{[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number365-07-1
SMILES
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O
InChI Identifier
InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
InChI KeyGYOZYWVXFNDGLU-XLPZGREQSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Deoxyribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Deoxyribonucleotides(KEGG)
  • Pyrimidine Deoxyribonucleotides
  • thymidine 5'-monophosphate(ChEBI)
Substituents
  • Hydropyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct ParentPyrimidine 2'-deoxyribonucleoside Monophosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pyrimidine metabolism
  • DNA component
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility6.78 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.7ALOGPS
pKa (strongest acidic)1.23ChemAxon
pKa (strongest basic)-3.2ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count4ChemAxon
polar surface area145.63ChemAxon
rotatable bond count4ChemAxon
refractivity66.28ChemAxon
polarizability27.58ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
  • Lysosome
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Pyrimidine MetabolismSMP00046map00240
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022499
KNApSAcK IDNot Available
Chemspider ID9319
KEGG Compound IDC00364
BioCyc IDTMP
BiGG ID34753
Wikipedia LinkdTMP
NuGOwiki LinkHMDB01227
Metagene LinkHMDB01227
METLIN ID6092
PubChem Compound9700
PDB IDDT
ChEBI ID17013
References
Synthesis ReferenceScarano, E. Enzymic formation of thymidylic acid from 5-methyl-5'-deoxycytidylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 945.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gribaudo G, Riera L, Caposio P, Maley F, Landolfo S: Human cytomegalovirus requires cellular deoxycytidylate deaminase for replication in quiescent cells. J Gen Virol. 2003 Jun;84(Pt 6):1437-41. Pubmed: 12771412
  2. Seno T, Ayusawa D, Shimizu K, Koyama H, Takeishi K, Hori T: Thymineless death and genetic events in mammalian cells. Basic Life Sci. 1985;31:241-63. Pubmed: 3888175
  3. Terai C, Carson DA: Pyrimidine nucleotide and nucleic acid synthesis in human monocytes and macrophages. Exp Cell Res. 1991 Apr;193(2):375-81. Pubmed: 1706277
  4. Gribaudo G, Riera L, Lembo D, De Andrea M, Gariglio M, Rudge TL, Johnson LF, Landolfo S: Murine cytomegalovirus stimulates cellular thymidylate synthase gene expression in quiescent cells and requires the enzyme for replication. J Virol. 2000 Jun;74(11):4979-87. Pubmed: 10799571

Enzymes

Gene Name:
NT5E
Uniprot ID:
P21589
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
DTYMK
Uniprot ID:
P23919
Reactions
Adenosine triphosphate + 5-Thymidylic acid unknown ADP + dTDPdetails
Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
dTDP + Water unknown 5-Thymidylic acid + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
dTDP + Water unknown 5-Thymidylic acid + Phosphoric aciddetails
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
NT5C2
Uniprot ID:
P49902
Reactions
5-Thymidylic acid + Water unknown Thymidine + Phosphoric aciddetails
Gene Name:
TK1
Uniprot ID:
P04183
Reactions
Adenosine triphosphate + Thymidine unknown ADP + 5-Thymidylic aciddetails
Gene Name:
TK2
Uniprot ID:
O00142
Reactions
Adenosine triphosphate + Thymidine unknown ADP + 5-Thymidylic aciddetails
Gene Name:
TYMS
Uniprot ID:
P04818
Reactions
5,10-Methylene-THF + dUMP unknown Dihydrofolic acid + 5-Thymidylic aciddetails
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Reactions
dTDP + Water unknown 5-Thymidylic acid + Phosphoric aciddetails
Gene Name:
Not Available
Uniprot ID:
Q8IZR3