Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H15N2O8P |
| Molecular Weight | 322.2085 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O
InChI
InChIKey=GYOZYWVXFNDGLU-XLPZGREQSA-N
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
| Molecular Formula | C10H15N2O8P |
| Molecular Weight | 322.2085 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
THYMIDINE 5'-MONOPHOSPHATE (or thymidine monophosphate, or TMP), a substrate of thymidylate kinase, transforms into the thymidine diphosphate that is essential in both the de novo and salvage pathways of DNA synthesis of the thymidine triphosphate. In mammalian cells, thymidine deprivation induces chromosome aberrations such as chromatid breaks, chromatid interchanges, and chromosome fragmentation.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Enzymatic and structural analysis of inhibitors designed against Mycobacterium tuberculosis thymidylate kinase. New insights into the phosphoryl transfer mechanism. | 2003-02-14 |
|
| Highly selective binding of organometallic ruthenium ethylenediamine complexes to nucleic acids: novel recognition mechanisms. | 2003-01-08 |
|
| Detection of thymidylate synthase modulators by a novel screening assay. | 2003-01 |
|
| Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase. | 2003-01 |
|
| Pre-clinical safety evaluation of novel nucleoside analogue-based dual-function microbicides (WHI-05 and WHI-07). | 2002-12 |
|
| Metabolism of stavudine-5'-[p-bromophenyl methoxyalaninyl phosphate], stampidine, in mice, dogs, and cats. | 2002-12 |
|
| The catalytic domains of thiamine triphosphatase and CyaB-like adenylyl cyclase define a novel superfamily of domains that bind organic phosphates. | 2002-11-27 |
|
| Gene therapy for intraperitoneally disseminated pancreatic cancers by Escherichia coli uracil phosphoribosiltransferase (UPRT) gene mediated by restricted replication-competent adenoviral vectors. | 2002-11-01 |
|
| Multidrug-resistant HIV-1 reverse transcriptase: involvement of ribonucleotide-dependent phosphorolysis in cross-resistance to nucleoside analogue inhibitors. | 2002-10-18 |
|
| Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses. | 2002-10-11 |
|
| Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase. | 2002-10-07 |
|
| Transcriptional analysis of genes encoding enzymes of the folate pathway in the human malaria parasite Plasmodium falciparum. | 2002-10 |
|
| Two-year toxicity and carcinogenicity studies in B(6)C(3)F(1) mice with 5-bromo-6-methoxy-5,6-dihydro-3'-azidothymidine-5'-(p-bromophenyl) methoxyalaninyl phosphate (WHI-07), a novel anti-HIV and contraceptive agent. | 2002-09-30 |
|
| Evidence for direct attack by hydroxide in phosphodiester hydrolysis. | 2002-09-18 |
|
| Crystal structure of Haemophilus influenzae NadR protein. A bifunctional enzyme endowed with NMN adenyltransferase and ribosylnicotinimide kinase activities. | 2002-09-06 |
|
| dUTPase and uracil-DNA glycosylase are central modulators of antifolate toxicity in Saccharomyces cerevisiae. | 2002-09-01 |
|
| Thymidylate synthase: a novel genetic determinant of plasma homocysteine and folate levels. | 2002-09 |
|
| Chimeric polypeptide of thymidine kinase and thymidylate kinase of shrimp white spot syndrome virus: thymidine kinase activity of the recombinant protein expressed in a baculovirus/insect cell system. | 2002-08-01 |
|
| Kinetic studies of human tyrosyl-DNA phosphodiesterase, an enzyme in the topoisomerase I DNA repair pathway. | 2002-08 |
|
| The means to an end of tumor cell resistance to chemotherapeutic drugs targeting thymidylate synthase: shoot the messenger. | 2002-08 |
|
| Protein expression profiles indicative for drug resistance of non-small cell lung cancer. | 2002-07-29 |
|
| Structure-based studies on species-specific inhibition of thymidylate synthase. | 2002-07-18 |
|
| Novel aspects of resistance to drugs targeted to dihydrofolate reductase and thymidylate synthase. | 2002-07-18 |
|
| Biochemistry. DNA building block reinvented. | 2002-07-05 |
|
| An alternative flavin-dependent mechanism for thymidylate synthesis. | 2002-07-05 |
|
| Bicyclic pyrimidine nucleoside analogues (BCNAs) as highly selective and potent inhibitors of varicella-zoster virus replication. | 2002-07 |
|
| Can a mixed damage interfere with DNA-protein cross-links repair? | 2002-06-18 |
|
| Database searching for thymidine and thymidylate kinase inhibitors using three-dimensional structure-based methods. | 2002-06 |
|
| Raltitrexed in the treatment of elderly patients with advanced colorectal cancer: an active and low toxicity regimen. | 2002-06 |
|
| The A167Y mutation converts the herpes simplex virus type 1 thymidine kinase into a guanosine analogue kinase. | 2002-05-21 |
|
| [Oxaliplatin: combinations with thymidylate synthetase inhibitors: two consecutive phase II studies]. | 2002-05-09 |
|
| Schedule-selective biochemical modulation of 5-fluorouracil in advanced colorectal cancer--a phase II study. | 2002-05-02 |
|
| Molecular phylogenetic study of Theileria sp. (Thung Song) based on the thymidylate synthetase gene. | 2002-05 |
|
| Biochemical and behavioral characterization of novel methylphenidate analogs. | 2002-05 |
|
| Hydrolysis of the 5'-p-nitrophenyl ester of TMP by the proofreading exonuclease (epsilon) subunit of Escherichia coli DNA polymerase III. | 2002-04-23 |
|
| Impact of the oxaliplatin-5 fluorouracil-folinic acid combination on respective intracellular determinants of drug activity. | 2002-04-08 |
|
| Interaction of pemetrexed disodium (ALIMTA, multitargeted antifolate) and irradiation in vitro. | 2002-04-01 |
|
| Hyper-processive and slower DNA chain elongation catalysed by DNA polymerase III holoenzyme purified from the dnaE173 mutator mutant of Escherichia coli. | 2002-04 |
|
| Cryophotolysis of caged compounds: a technique for trapping intermediate states in protein crystals. | 2002-04 |
|
| The genome of bacteriophage phiKZ of Pseudomonas aeruginosa. | 2002-03-15 |
|
| Ethanol decreases the efficiency of phosphorylation of thymidine kinase in a human T-lymphocytic cell line. | 2002-03 |
|
| Role of a novel soluble nucleotide phospho-hydrolase from sheep plasma in inhibition of platelet reactivity: hemostasis, thrombosis, and vascular biology. | 2002-02 |
|
| Synergistic cytotoxic effect between serine-threonine phosphatase inhibitors and 5-fluorouracil: a novel concept for modulation of cytotoxic effect. | 2002-02 |
|
| Methylenetetrahydrofolate reductase polymorphism and susceptibility to breast cancer. | 2002 |
|
| Involvement of a substrate cycle between thymidine and thymidylate in the regulation of DNA precursor pool in ehrlich ascites tumour. | 2002 |
|
| Electrospray ionization mass spectrometry of serine/alanine conjugated 5'-UMP and 3',5'-dithymidine phosphoramidates. | 2002 |
|
| Prognostic significance of the thymidylate biosynthetic enzymes in human colorectal tumors. | 2002 |
|
| Raltitrexed (Tomudex) administration in patients with relapsed metastatic colorectal cancer after weekly irinotecan/5-Fluorouracil/Leucovorin chemotherapy. | 2002 |
|
| Polymorphic sequences of the tyrosinase gene: allele analysis on 16 OCA1 patients in Japan indicate that three polymorphic sequences in the tyrosinase gene promoter could be powerful markers for indirect gene diagnosis. | 2002 |
|
| The role of dUTPase and uracil-DNA repair in cancer chemotherapy. | 2001-12 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:45:43 GMT 2025
by
admin
on
Mon Mar 31 22:45:43 GMT 2025
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| Record UNII |
43W3021X6C
|
| Record Status |
Validated (UNII)
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| Record Version |
|
-
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Preferred Name | English | ||
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
532716
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admin on Mon Mar 31 22:45:43 GMT 2025 , Edited by admin on Mon Mar 31 22:45:43 GMT 2025
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46713
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365-07-1
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63528
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43W3021X6C
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Thymidine monophosphate
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9700
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17013
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