trabectedin   Click here for help

GtoPdb Ligand ID: 2774

Synonyms: ecteinascidin 743 | ET-743 | Yondelis®
Approved drug PDB Ligand
trabectedin is an approved drug (EMA (2007), FDA (2015))
Compound class: Natural product
Comment: The ecteinascidins (Ets) are natural products derived from the marine tunicate Ecteinascidia turbinata. Being a natural substance, there is some ambiguity in the literature as to the exact chemical structure of trabectedin, therefore representations of the compound on the external resource links may vary slightly from that shown here. Trabectedin is now produced synthetically. Mechanistically trabectedin is a DNA minor groove binder and it forms covalent bonds with the exocyclic amino group of certain guanines in the minor groove and interstrand crosslinks via van der Waals interactions and hydrogen bonds [2].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 CDK toolkit. 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 7
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 194.02
Molecular weight 761.26
XLogP 2.84
No. Lipinski's rules broken 0
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.

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Canonical SMILES COc1cc2c(cc1O)CCNC12CSC2c3c(OC(=O)C)c(C)c4c(c3C(COC1=O)N1C2C2N(C(C1O)Cc1c2c(O)c(c(c1)C)OC)C)OCO4
Isomeric SMILES COc1cc2c(cc1O)CCN[C@@]12CS[C@@H]2c3c(OC(=O)C)c(C)c4c(c3[C@H](COC1=O)N1[C@@H]2[C@@H]2N([C@H]([C@@H]1O)Cc1c2c(O)c(c(c1)C)OC)C)OCO4
InChI InChI=1S/C39H43N3O11S/c1-16-9-20-10-22-37(46)42-23-13-50-38(47)39(21-12-25(48-5)24(44)11-19(21)7-8-40-39)14-54-36(30(42)29(41(22)4)26(20)31(45)32(16)49-6)28-27(23)35-34(51-15-52-35)17(2)33(28)53-18(3)43/h9,11-12,22-23,29-30,36-37,40,44-46H,7-8,10,13-15H2,1-6H3/t22-,23-,29+,30+,36+,37-,39+/m0/s1
InChI Key PKVRCIRHQMSYJX-AIFWHQITSA-N
Classification Click here for help
Compound class Natural product
Approved drug? Yes (EMA (2007), FDA (2015))
International Nonproprietary Names Click here for help
INN number INN
8206 trabectedin
Synonyms Click here for help
ecteinascidin 743 | ET-743 | Yondelis®
Database Links Click here for help
CAS Registry No. 114899-77-3
ChEBI CHEBI:84050
ChEMBL Ligand CHEMBL450449
DrugBank Ligand DB05109
DrugCentral Ligand 4633
GtoPdb PubChem SID 135652680
PubChem CID 108150
RCSB PDB Ligand ECT
Search Google for chemical match using the InChIKey PKVRCIRHQMSYJX-AIFWHQITSA-N
Search Google for chemicals with the same backbone PKVRCIRHQMSYJX
Search PubMed clinical trials trabectedin
Search PubMed titles trabectedin
Search PubMed titles/abstracts trabectedin
UniChem Compound Search for chemical match using the InChIKey PKVRCIRHQMSYJX-AIFWHQITSA-N
UniChem Connectivity Search for chemical match using the InChIKey PKVRCIRHQMSYJX-AIFWHQITSA-N
Wikipedia Trabectedin