Common NameDtmp
Description5-Thymidylic acid (conjugate base thymidylate), also known as thymidine monophosphate (TMP), deoxythymidine monophosphate (dTMP), or deoxythymidylic acid (conjugate base deoxythymidylate), is a nucleotide that is used as a monomer in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. dTMP consists of a phosphate group, the pentose sugar deoxyribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine monophosphate often does not contain the "deoxy" prefix in its name; nevertheless, its symbol often includes a "d" ("dTMP"). 5-Thymidylic acid belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. The neutral species of 5-Thymidylic acid (2'-deoxythymidine 5'-monophosphate). 5-Thymidylic acid exists in all living species, ranging from bacteria to humans. Within humans, 5-thymidylic acid participates in a number of enzymatic reactions. In particular, 5-thymidylic acid and dihydrofolic acid can be biosynthesized from dUMP and 5,10-methylene-THF by the enzyme thymidylate synthase. In addition, 5-thymidylic acid can be converted into dTDP; which is catalyzed by the enzyme thymidylate synthase. In humans, 5-thymidylic acid is involved in pyrimidine metabolism. Outside of the human body, 5-Thymidylic acid has been detected, but not quantified in several different foods, such as common buckwheats, corn salad, garden cress, squashberries, and star fruits.
Structure
Molecular FormulaC10H15N2O8P
Average Mass322.20850
Monoisotopic Mass322.05660
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 Name[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-3h-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number0365-07-01
SMILESCc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)([O-])[O-])O2)c(=O)[nH]c1=O
InChI IdentifierInChI=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
CHEBI IDCHEBI:63528
HMDB IDHMDB0001227
Pathways
NameSMPDB/PathBank
Pyrimidine metabolism
Beta Ureidopropionase Deficiency
Dihydropyrimidinase Deficiency
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
UMP Synthase Deficiency (Orotic Aciduria)
StateSolid
Water Solubility6.78e+00 g/l
logP-1.37
logS-1.68
pKa (Strongest Acidic)1.23
pKa (Strongest Basic)-3.24
Hydrogen Acceptor Count7
Hydrogen Donor Count4
Polar Surface Area145.63 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity66.28 m³·mol⁻¹
Polarizability27.58

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