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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15N2O8P
Molecular Weight 322.2089
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THYMIDINE 5'-MONOPHOSPHATE

SMILES

Cc1cn([C@@]2([H])C[C@@]([H])([C@@]([H])(COP(=O)(O)O)O2)O)c(=O)nc1O

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

HIDE SMILES / InChI

Molecular Formula C10H15N2O8P
Molecular Weight 322.2089
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
15500.0 nM [Ki]
4500.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Quod erat demonstrandum? The mystery of experimental validation of apparently erroneous computational analyses of protein sequences.
2001
Can a mixed damage interfere with DNA-protein cross-links repair?
2001 Apr-Jun
The role of dUTPase and uracil-DNA repair in cancer chemotherapy.
2001 Dec
Dinucleotide microsatellites from Eucalyptus sieberi: inheritance, diversity, and improved scoring of single-base differences.
2001 Dec
[Oxaliplatin: combinations with thymidylate synthetase inhibitors: two consecutive phase II studies].
2001 Nov-Dec
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
Hyper-processive and slower DNA chain elongation catalysed by DNA polymerase III holoenzyme purified from the dnaE173 mutator mutant of Escherichia coli.
2002 Apr
Cryophotolysis of caged compounds: a technique for trapping intermediate states in protein crystals.
2002 Apr
Interaction of pemetrexed disodium (ALIMTA, multitargeted antifolate) and irradiation in vitro.
2002 Apr 1
Hydrolysis of the 5'-p-nitrophenyl ester of TMP by the proofreading exonuclease (epsilon) subunit of Escherichia coli DNA polymerase III.
2002 Apr 23
Impact of the oxaliplatin-5 fluorouracil-folinic acid combination on respective intracellular determinants of drug activity.
2002 Apr 8
Kinetic studies of human tyrosyl-DNA phosphodiesterase, an enzyme in the topoisomerase I DNA repair pathway.
2002 Aug
The means to an end of tumor cell resistance to chemotherapeutic drugs targeting thymidylate synthase: shoot the messenger.
2002 Aug
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 Aug 1
Pre-clinical safety evaluation of novel nucleoside analogue-based dual-function microbicides (WHI-05 and WHI-07).
2002 Dec
Metabolism of stavudine-5'-[p-bromophenyl methoxyalaninyl phosphate], stampidine, in mice, dogs, and cats.
2002 Dec
Role of a novel soluble nucleotide phospho-hydrolase from sheep plasma in inhibition of platelet reactivity: hemostasis, thrombosis, and vascular biology.
2002 Feb
Synergistic cytotoxic effect between serine-threonine phosphatase inhibitors and 5-fluorouracil: a novel concept for modulation of cytotoxic effect.
2002 Feb
Specific recognition of the bicyclic pyrimidine nucleoside analogs, a new class of highly potent and selective inhibitors of varicella-zoster virus (VZV), by the VZV-encoded thymidine kinase.
2002 Feb
Long-read pyrosequencing using pure 2'-deoxyadenosine-5'-O'-(1-thiotriphosphate) Sp-isomer.
2002 Feb 1
Structure-based studies on species-specific inhibition of thymidylate synthase.
2002 Jul 18
Novel aspects of resistance to drugs targeted to dihydrofolate reductase and thymidylate synthase.
2002 Jul 18
Protein expression profiles indicative for drug resistance of non-small cell lung cancer.
2002 Jul 29
Biochemistry. DNA building block reinvented.
2002 Jul 5
Database searching for thymidine and thymidylate kinase inhibitors using three-dimensional structure-based methods.
2002 Jun
Raltitrexed in the treatment of elderly patients with advanced colorectal cancer: an active and low toxicity regimen.
2002 Jun
Ethanol decreases the efficiency of phosphorylation of thymidine kinase in a human T-lymphocytic cell line.
2002 Mar
Biochemical and behavioral characterization of novel methylphenidate analogs.
2002 May
Schedule-selective biochemical modulation of 5-fluorouracil in advanced colorectal cancer--a phase II study.
2002 May 2
The A167Y mutation converts the herpes simplex virus type 1 thymidine kinase into a guanosine analogue kinase.
2002 May 21
Gene therapy for intraperitoneally disseminated pancreatic cancers by Escherichia coli uracil phosphoribosiltransferase (UPRT) gene mediated by restricted replication-competent adenoviral vectors.
2002 Nov 1
The catalytic domains of thiamine triphosphatase and CyaB-like adenylyl cyclase define a novel superfamily of domains that bind organic phosphates.
2002 Nov 27
Transcriptional analysis of genes encoding enzymes of the folate pathway in the human malaria parasite Plasmodium falciparum.
2002 Oct
Cytoplasmic serine hydroxymethyltransferase mediates competition between folate-dependent deoxyribonucleotide and S-adenosylmethionine biosyntheses.
2002 Oct 11
Multidrug-resistant HIV-1 reverse transcriptase: involvement of ribonucleotide-dependent phosphorolysis in cross-resistance to nucleoside analogue inhibitors.
2002 Oct 18
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
2002 Oct 7
Thymidylate synthase: a novel genetic determinant of plasma homocysteine and folate levels.
2002 Sep
dUTPase and uracil-DNA glycosylase are central modulators of antifolate toxicity in Saccharomyces cerevisiae.
2002 Sep 1
Evidence for direct attack by hydroxide in phosphodiester hydrolysis.
2002 Sep 18
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 Sep 30
Crystal structure of Haemophilus influenzae NadR protein. A bifunctional enzyme endowed with NMN adenyltransferase and ribosylnicotinimide kinase activities.
2002 Sep 6
Enzymatic and structural analysis of inhibitors designed against Mycobacterium tuberculosis thymidylate kinase. New insights into the phosphoryl transfer mechanism.
2003 Feb 14
Detection of thymidylate synthase modulators by a novel screening assay.
2003 Jan
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 Jan
Highly selective binding of organometallic ruthenium ethylenediamine complexes to nucleic acids: novel recognition mechanisms.
2003 Jan 8
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:17:42 UTC 2021
Edited
by admin
on Sat Jun 26 12:17:42 UTC 2021
Record UNII
43W3021X6C
Record Status Validated (UNII)
Record Version
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Name Type Language
THYMIDINE 5'-MONOPHOSPHATE
Systematic Name English
THYMIDINE MONONUCLEOTIDE
Common Name English
TMP (NUCLEOTIDE)
Common Name English
NSC-46713
Code English
DTMP
Common Name English
DEOXYTHYMIDINE MONOPHOSPHATE
Systematic Name English
5'-THYMIDYLIC ACID
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 532716
Created by admin on Sat Jun 26 12:17:42 UTC 2021 , Edited by admin on Sat Jun 26 12:17:42 UTC 2021
Code System Code Type Description
DRUG BANK
DB01643
Created by admin on Sat Jun 26 12:17:42 UTC 2021 , Edited by admin on Sat Jun 26 12:17:42 UTC 2021
PRIMARY
CAS
365-07-1
Created by admin on Sat Jun 26 12:17:42 UTC 2021 , Edited by admin on Sat Jun 26 12:17:42 UTC 2021
PRIMARY
FDA UNII
43W3021X6C
Created by admin on Sat Jun 26 12:17:42 UTC 2021 , Edited by admin on Sat Jun 26 12:17:42 UTC 2021
PRIMARY
PUBCHEM
9700
Created by admin on Sat Jun 26 12:17:42 UTC 2021 , Edited by admin on Sat Jun 26 12:17:42 UTC 2021
PRIMARY