Identification
- Generic Name
- 5-Iodouracil
- DrugBank Accession Number
- DB03554
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5-Iodouracil (DB03554)
- Weight
- Average: 237.9833
Monoisotopic: 237.92392077 - Chemical Formula
- C4H3IN2O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UDihydropyrimidine dehydrogenase [NADP(+)] Not Available Humans - 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Halopyrimidines
- Alternative Parents
- Pyrimidones / Hydropyrimidines / Aryl iodides / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds show 4 more
- Substituents
- Aromatic heteromonocyclic compound / Aryl halide / Aryl iodide / Azacycle / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organoiodine compound (CHEBI:43636)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- H59BRK500M
- CAS number
- 696-07-1
- InChI Key
- KSNXJLQDQOIRIP-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H3IN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
- IUPAC Name
- 5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- IC1=CNC(=O)NC1=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 69672
- PubChem Substance
- 46507512
- ChemSpider
- 62873
- BindingDB
- 50124203
- ChEBI
- 43636
- ChEMBL
- CHEMBL1173
- ZINC
- ZINC000001092752
- PDBe Ligand
- IUR
- PDB Entries
- 1gte / 1gth / 2wk6 / 7pcp
Clinical Trials
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 8.12 mg/mL ALOGPS logP -0.07 ALOGPS logP 0.13 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 7.55 Chemaxon pKa (Strongest Basic) -6.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.2 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 39.32 m3·mol-1 Chemaxon Polarizability 14.65 Å3 Chemaxon Number of Rings 1 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 + 0.819 Blood Brain Barrier + 0.9681 Caco-2 permeable - 0.7515 P-glycoprotein substrate Non-substrate 0.7821 P-glycoprotein inhibitor I Non-inhibitor 0.9234 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.904 CYP450 2C9 substrate Non-substrate 0.7677 CYP450 2D6 substrate Non-substrate 0.8957 CYP450 3A4 substrate Non-substrate 0.7543 CYP450 1A2 substrate Non-inhibitor 0.7846 CYP450 2C9 inhibitor Non-inhibitor 0.9545 CYP450 2D6 inhibitor Non-inhibitor 0.9184 CYP450 2C19 inhibitor Non-inhibitor 0.9638 CYP450 3A4 inhibitor Non-inhibitor 0.9526 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.98 Ames test Non AMES toxic 0.8918 Carcinogenicity Non-carcinogens 0.9402 Biodegradation Not ready biodegradable 0.925 Rat acute toxicity 2.0643 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9568 hERG inhibition (predictor II) Non-inhibitor 0.9472
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00kr-2980000000-f57c013b694410848702 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0190000000-613da22aff65566b7c84 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014v-1920000000-bf9d244e36be9fb30218 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000l-4090000000-87af1b5733c4d5b62fb3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-30f66c8f5ba7d380d3c1 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fr6-5900000000-0af4f13145c88bb148ea Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-d7d271b88a73c99565c7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.56303 predictedDeepCCS 1.0 (2019) [M+H]+ 130.93282 predictedDeepCCS 1.0 (2019) [M+Na]+ 139.73964 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein homodimerization activity
- Specific Function
- Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
- Gene Name
- DPYD
- Uniprot ID
- Q12882
- Uniprot Name
- Dihydropyrimidine dehydrogenase [NADP(+)]
- Molecular Weight
- 111400.32 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]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52