estramustine   Click here for help

GtoPdb Ligand ID: 9076

Synonyms: Emcyt® | Estracyt®
Approved drug
estramustine is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: Estramustine is a synthetic analogue combining estradiol and nornitrogen mustard. It is a DNA alkylating agent with antineoplastic activity.
Marketed formulations contain estramustine phosphate sodium (PubChem CID 444000).
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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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Click here for structure editor
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 1
Rotatable bonds 7
Topological polar surface area 49.77
Molecular weight 439.17
XLogP 5.74
No. Lipinski's rules broken 1

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(C(=O)Oc1ccc2c(c1)CCC1C2CCC2(C1CCC2O)C)CCCl
Isomeric SMILES ClCCN(C(=O)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)CCCl
InChI InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
InChI Key FRPJXPJMRWBBIH-RBRWEJTLSA-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 (FDA (1981))
IUPAC Name Click here for help
[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
International Nonproprietary Names Click here for help
INN number INN
2877 estramustine
Synonyms Click here for help
Emcyt® | Estracyt®
Database Links Click here for help
BindingDB Ligand 50333646
ChEMBL Ligand CHEMBL1575
DrugBank Ligand DB01196
DrugCentral Ligand 1065
GtoPdb PubChem SID 315661161
LIPID MAPS LMST02010038
PubChem CID 259331
Search Google for chemical match using the InChIKey FRPJXPJMRWBBIH-RBRWEJTLSA-N
Search Google for chemicals with the same backbone FRPJXPJMRWBBIH
Search PubMed clinical trials estramustine
Search PubMed titles estramustine
Search PubMed titles/abstracts estramustine
UniChem Compound Search for chemical match using the InChIKey FRPJXPJMRWBBIH-RBRWEJTLSA-N
UniChem Connectivity Search for chemical match using the InChIKey FRPJXPJMRWBBIH-RBRWEJTLSA-N
Wikipedia Estramustine