2'-Deoxyuridine
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Identification
- Generic Name
- 2'-Deoxyuridine
- DrugBank Accession Number
- DB02256
- Background
2'-Deoxyuridine. An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 228.202
Monoisotopic: 228.074621504 - Chemical Formula
- C9H12N2O5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UUridine phosphorylase Not Available Escherichia coli (strain K12) UThymidylate synthase Not Available Escherichia coli (strain K12) - 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
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleosides
- Sub Class
- Pyrimidine 2'-deoxyribonucleosides
- Direct Parent
- Pyrimidine 2'-deoxyribonucleosides
- Alternative Parents
- Pyrimidones / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols / Lactams / Oxacyclic compounds / Azacyclic compounds show 5 more
- Substituents
- Alcohol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrimidine 2'-deoxyribonucleoside (CHEBI:16450) / Deoxyribonucleosides (C00526)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- W78I7AY22C
- CAS number
- 951-78-0
- InChI Key
- MXHRCPNRJAMMIM-SHYZEUOFSA-N
- InChI
- InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
- IUPAC Name
- 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O
References
- Synthesis Reference
Kenzo Watanabe, Yoshinori Kato, Masahiko Saito, Takeo Oba, Hisashi Fukushima, Takeshi Hara, "5-fluoro-2'-deoxyuridine derivatives and a process for the preparation thereof." U.S. Patent US4605645, issued May, 1984.
US4605645- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000012
- KEGG Compound
- C00526
- PubChem Compound
- 13712
- PubChem Substance
- 46506680
- ChemSpider
- 13118
- ChEBI
- 16450
- ChEMBL
- CHEMBL353955
- ZINC
- ZINC000000155696
- PDBe Ligand
- DUR
- PDB Entries
- 1bdu / 1oe5 / 1rxs / 1tdu / 2c53 / 2i7d / 2yb0 / 3kuk / 4aoo / 4aoz … show 7 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 163 °C PhysProp logP -1.51 BALZARINI,JM ET AL. (1989) - Predicted Properties
Property Value Source Water Solubility 90.6 mg/mL ALOGPS logP -1.5 ALOGPS logP -1.5 Chemaxon logS -0.4 ALOGPS pKa (Strongest Acidic) 9.71 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 99.1 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 51.05 m3·mol-1 Chemaxon Polarizability 21.06 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 + 0.9512 Blood Brain Barrier + 0.7655 Caco-2 permeable - 0.8937 P-glycoprotein substrate Non-substrate 0.7208 P-glycoprotein inhibitor I Non-inhibitor 0.8877 P-glycoprotein inhibitor II Non-inhibitor 0.8561 Renal organic cation transporter Non-inhibitor 0.8954 CYP450 2C9 substrate Non-substrate 0.7602 CYP450 2D6 substrate Non-substrate 0.8792 CYP450 3A4 substrate Non-substrate 0.5493 CYP450 1A2 substrate Non-inhibitor 0.9479 CYP450 2C9 inhibitor Non-inhibitor 0.9459 CYP450 2D6 inhibitor Non-inhibitor 0.9491 CYP450 2C19 inhibitor Non-inhibitor 0.9499 CYP450 3A4 inhibitor Non-inhibitor 0.9249 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.949 Ames test Non AMES toxic 0.8635 Carcinogenicity Non-carcinogens 0.8101 Biodegradation Ready biodegradable 0.5723 Rat acute toxicity 1.8101 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9411 hERG inhibition (predictor II) Non-inhibitor 0.8765
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 159.4685066 predictedDarkChem Lite v0.1.0 [M-H]- 150.3923667 predictedDarkChem Standard v0.1.0 [M-H]- 159.1811066 predictedDarkChem Lite v0.1.0 [M-H]- 152.83492 predictedDeepCCS 1.0 (2019) [M+H]+ 162.2327066 predictedDarkChem Lite v0.1.0 [M+H]+ 161.3545066 predictedDarkChem Lite v0.1.0 [M+H]+ 160.8331066 predictedDarkChem Lite v0.1.0 [M+H]+ 155.23045 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.5130066 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.5286533 predictedDarkChem Standard v0.1.0 [M+Na]+ 159.9011066 predictedDarkChem Lite v0.1.0 [M+Na]+ 161.14305 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsUridine phosphorylase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Uridine phosphorylase activity
- Specific Function
- Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources ...
- Gene Name
- udp
- Uniprot ID
- P12758
- Uniprot Name
- Uridine phosphorylase
- Molecular Weight
- 27158.88 Da
References
2. DetailsThymidylate synthase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Thymidylate synthase activity
- Specific Function
- Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
- Gene Name
- thyA
- Uniprot ID
- P0A884
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 30479.475 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52