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uramustine   Click here for help

GtoPdb Ligand ID: 7621

Synonyms: U-8344 | Uracil Mustard®
Approved drug
uramustine is an approved drug
Compound class: Synthetic organic
Comment: Chemically uramustine is a derivative of nitrogen mustard and uracil. It is used clinically as a DNA alkylating anti-cancer chemotherapeutic.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 68.96
Molecular weight 251.02
XLogP 1.56
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
Isomeric SMILES ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
InChI InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
InChI Key IDPUKCWIGUEADI-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
5-[bis(2-chloroethyl)amino]-1H-pyrimidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
1351 uramustine
Synonyms Click here for help
U-8344 | Uracil Mustard®
Database Links Click here for help
CAS Registry No. 66-75-1
ChEMBL Ligand CHEMBL1488
DrugBank Ligand DB00791
DrugCentral Ligand 2795
GtoPdb PubChem SID 223365956
PubChem CID 6194
Search Google for chemical match using the InChIKey IDPUKCWIGUEADI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IDPUKCWIGUEADI
Search PubMed clinical trials uramustine
Search PubMed titles uramustine
Search PubMed titles/abstracts uramustine
UniChem Compound Search for chemical match using the InChIKey IDPUKCWIGUEADI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IDPUKCWIGUEADI-UHFFFAOYSA-N
Wikipedia Uramustine