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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2D Structure
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Physico-chemical Properties
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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
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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
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
ChEMBL Ligand CHEMBL450449
DrugBank Ligand DB05109
DrugCentral Ligand 4633
GtoPdb PubChem SID 135652680
PubChem CID 108150
Search Google for chemical match using the InChIKey PKVRCIRHQMSYJX-AIFWHQITSA-N
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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