Identification
- Generic Name
- Thymidine monophosphate
- DrugBank Accession Number
- DB01643
- Background
5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Thymidine monophosphate (DB01643)
- Weight
- Average: 322.2085
Monoisotopic: 322.056601978 - Chemical Formula
- C10H15N2O8P
- Synonyms
- 2'-deoxy-5-methyluridine 5'-(dihydrogen phosphate)
- 5-Methyl-dUMP
- 5'-Thymidylic acid
- 5'-TMP
- Deoxyribosylthymine monophosphate
- Deoxythymidine monophosphate
- dTMP
- ribothymidine 5'-monophosphate
- thymidine 5'-(dihydrogen phosphate)
- Thymidine 5'-phosphate
- Thymidine 5'-phosphoric acid
- Thymidine mononucleotide
- Thymidine monophosphate
- Thymidine-5'-Monophosphate
- Thymidine-5'-monophosphoric acid
- Thymidine-5'-phosphate
- Thymidylate
- Thymidylic acid
- TMP
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UThymidylate kinase product ofMycobacterium tuberculosis UThymidylate kinase product ofHumans UThymidylate synthase product ofHumans UDNA topoisomerase 1 Not Available Escherichia coli (strain K12) UThymidylate synthase product ofLactobacillus casei UPCZA361.16 Not Available Amycolatopsis orientalis UDNA polymerase III subunit epsilon Not Available Escherichia coli (strain K12) UGlucose-1-phosphate thymidylyltransferase Not Available Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Pyrimidine Metabolism Metabolic MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) Disease beta-Ureidopropionase Deficiency Disease Dihydropyrimidinase Deficiency Disease UMP Synthase Deficiency (Orotic Aciduria) Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleotides
- Sub Class
- Pyrimidine deoxyribonucleotides
- Direct Parent
- Pyrimidine 2'-deoxyribonucleoside monophosphates
- Alternative Parents
- Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols / Lactams / Oxacyclic compounds show 5 more
- Substituents
- Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Monoalkyl phosphate / Organic nitrogen compound show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- thymidine 5'-monophosphate (CHEBI:17013) / Deoxyribonucleotides (C00364)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 43W3021X6C
- CAS number
- 365-07-1
- InChI Key
- GYOZYWVXFNDGLU-XLPZGREQSA-N
- InChI
- 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
- 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
- SMILES
- CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O
References
- Synthesis Reference
Timothy Benson, "Crystallization and structure determination of staphylococcus aureus thymidylate kinase." U.S. Patent US20040171050, issued September 02, 2004.
US20040171050- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001227
- KEGG Compound
- C00364
- PubChem Compound
- 9700
- PubChem Substance
- 46504719
- ChemSpider
- 9319
- BindingDB
- 50332929
- ChEBI
- 17013
- ChEMBL
- CHEMBL394429
- ZINC
- ZINC000001678872
- PDBe Ligand
- DT
- Wikipedia
- Thymidine_monophosphate
- PDB Entries
- 1cy1 / 1cy2 / 1cy4 / 1cy7 / 1cy8 / 1e2d / 1e2e / 1e2f / 1e2g / 1e2q … show 72 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 6.78 mg/mL ALOGPS logP -1.4 ALOGPS logP -1.2 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.23 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 145.63 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 66.28 m3·mol-1 Chemaxon Polarizability 27.46 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6163 Blood Brain Barrier + 0.7483 Caco-2 permeable - 0.7958 P-glycoprotein substrate Non-substrate 0.622 P-glycoprotein inhibitor I Non-inhibitor 0.7939 P-glycoprotein inhibitor II Non-inhibitor 0.9698 Renal organic cation transporter Non-inhibitor 0.9135 CYP450 2C9 substrate Non-substrate 0.6352 CYP450 2D6 substrate Non-substrate 0.8525 CYP450 3A4 substrate Substrate 0.5394 CYP450 1A2 substrate Non-inhibitor 0.8991 CYP450 2C9 inhibitor Non-inhibitor 0.8806 CYP450 2D6 inhibitor Non-inhibitor 0.9153 CYP450 2C19 inhibitor Non-inhibitor 0.8753 CYP450 3A4 inhibitor Non-inhibitor 0.823 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9228 Ames test Non AMES toxic 0.618 Carcinogenicity Non-carcinogens 0.8044 Biodegradation Not ready biodegradable 0.6481 Rat acute toxicity 2.3169 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9424 hERG inhibition (predictor II) Non-inhibitor 0.8058
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.3356377 predictedDarkChem Lite v0.1.0 [M-H]- 187.0717377 predictedDarkChem Lite v0.1.0 [M-H]- 170.10721 predictedDeepCCS 1.0 (2019) [M+H]+ 181.7434377 predictedDarkChem Lite v0.1.0 [M+H]+ 189.0481377 predictedDarkChem Lite v0.1.0 [M+H]+ 172.46521 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.2138377 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.0566377 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.12582 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Catalyzes the reversible phosphorylation of deoxythymidine monophosphate (dTMP) to deoxythymidine diphosphate (dTDP), using ATP as its preferred phosphoryl donor. Situated at the junction of both de novo and salvage pathways of deoxythymidine triphosphate (dTTP) synthesis, is essential for DNA synthesis and cellular growth. Has a broad specificity for nucleoside triphosphates, being highly active with ATP or dATP as phosphate donors, and less active with ITP, GTP, CTP and UTP.
- Specific Function
- Atp binding
- Gene Name
- tmk
- Uniprot ID
- P9WKE1
- Uniprot Name
- Thymidylate kinase
- Molecular Weight
- 22634.285 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Uridylate kinase activity
- Specific Function
- Catalyzes the conversion of dTMP to dTDP.
- Gene Name
- DTYMK
- Uniprot ID
- P23919
- Uniprot Name
- Thymidylate kinase
- Molecular Weight
- 23819.105 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Thymidylate synthase activity
- Specific Function
- Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
- Gene Name
- TYMS
- Uniprot ID
- P04818
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 35715.65 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Magnesium ion binding
- Specific Function
- Releases the supercoiling and torsional tension of DNA, which is introduced during the DNA replication and transcription, by transiently cleaving and rejoining one strand of the DNA duplex. Introdu...
- Gene Name
- topA
- Uniprot ID
- P06612
- Uniprot Name
- DNA topoisomerase 1
- Molecular Weight
- 97349.0 Da
References
- Kind
- Protein
- Organism
- Lactobacillus casei
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Thymidylate synthase activity
- Specific Function
- Provides the sole de novo source of dTMP for DNA biosynthesis.
- Gene Name
- thyA
- Uniprot ID
- P00469
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 36579.235 Da
References
- Kind
- Protein
- Organism
- Amycolatopsis orientalis
- Pharmacological action
- Unknown
- General Function
- Dtdp-4-dehydrorhamnose 3,5-epimerase activity
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- O52806
- Uniprot Name
- PCZA361.16
- Molecular Weight
- 22488.53 Da
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. The epsilon subunit contain the editing function and is a proofreading 3'-5' exonuc...
- Gene Name
- dnaQ
- Uniprot ID
- P03007
- Uniprot Name
- DNA polymerase III subunit epsilon
- Molecular Weight
- 27098.7 Da
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
- Pharmacological action
- Unknown
- General Function
- Nucleotide binding
- Specific Function
- Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis.
- Gene Name
- rmlA
- Uniprot ID
- Q9HU22
- Uniprot Name
- Glucose-1-phosphate thymidylyltransferase
- Molecular Weight
- 32456.65 Da
Drug created at June 13, 2005 13:24 / Updated at April 30, 2023 10:33