trabectedin
AlkaPlorer ID: AK025875
Synonym: 'Ecteinascidin 743', 'Ecteinascidin', 'Ect 743', '(-)-Ecteinascidin 743', 'ET743', 'trabectedin', '114899-77-3', 'ET-743'
IUPAC Name: [(1R,2R,3R,11S,12S,14R,26R)-5,6',12-trihydroxy-6,7'-dimethoxy-7,21,30-trimethyl-27-oxospiro[17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaene-26,1'-3,4-dihydro-2H-isoquinoline]-22-yl] acetate
Structure
SMILES: COC1=CC2=C(C=C1O)CCN[C@]21CS[C@@H]2C3=C(OC(C)=O)C(C)=C4OCOC4=C3[C@H](COC1=O)N1[C@@H]2[C@H]2C3=C(O)C(OC)=C(C)C=C3C[C@@H]([C@@H]1O)N2C
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
InChIKey: PKVRCIRHQMSYJX-AIFWHQITSA-N
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Ecteinascidia turbinata | Ecteinascidia | Perophoridae | Phlebobranchia | Ascidiacea | Chordata | Metazoa | Eukaryota |
Properties Information
Molecule Weight: 761.8500000000001
TPSA？: 168.72
MolLogP？: 3.413240000000002
Number of H-Donors: 4
Number of H-Acceptors: 15
RingCount: 10
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Cricetulus griseus | CHO-AA8 | Activity | 20.0 | % | 10.1073/pnas.0609877104 |
| Cricetulus griseus | CHO-AA8 | Activity | 140.0 | nM | 10.1073/pnas.0609877104 |
| Cricetulus griseus | CHO-AA8 | Activity | nan | None | 10.1073/pnas.0609877104 |
| Cricetulus griseus | V79 | Activity | 0.0 | None | 10.1073/pnas.0609877104 |
| Cricetulus griseus | V79 | Activity | 1.0 | None | 10.1073/pnas.0609877104 |
| Cricetulus griseus | V79 | Activity | 24.0 | None | 10.1073/pnas.0609877104 |
| Cricetulus griseus | V79 | Activity | 27.0 | None | 10.1073/pnas.0609877104 |
| Cricetulus griseus | V79 | Activity | 50.0 | None | 10.1073/pnas.0609877104 |
| Cricetulus griseus | V79 | Activity | 57.0 | None | 10.1073/pnas.0609877104 |
| Homo sapiens | A549 | GI50 | 2.81 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | A549 | GI50 | 125.0 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | A549 | GI50 | 26300.0 | nM | 10.1021/np050247f |
| Homo sapiens | A549 | LC50 | 3.89 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | A549 | LC50 | 171.0 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | A549 | TGI | 3.15 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | A549 | TGI | 131.0 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | CCRF-CEM | Activity | nan | None | 10.1073/pnas.0609877104 |
| Homo sapiens | HeLa | Activity | 50.0 | % | 10.1073/pnas.0609877104 |
| Homo sapiens | HeLa | Activity | nan | None | 10.1073/pnas.0609877104 |
| Homo sapiens | HT-29 | GI50 | 22.0 | nM | 10.1016/j.bmc.2006.10.009 |
| Homo sapiens | HT-29 | GI50 | 51.7 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | HT-29 | GI50 | 2470.0 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | HT-29 | GI50 | 19700.0 | nM | 10.1021/np050247f |
| Homo sapiens | HT-29 | LC50 | 3550.0 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | HT-29 | LC50 | 100000000.0 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | HT-29 | TGI | 63.0 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | HT-29 | TGI | 2930.0 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | MDA-MB-231 | GI50 | 0.396 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | MDA-MB-231 | GI50 | 19.0 | nM | 10.1016/j.bmc.2006.10.009 |
| Homo sapiens | MDA-MB-231 | GI50 | 55.1 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | MDA-MB-231 | GI50 | 18400.0 | nM | 10.1021/np050247f |
| Homo sapiens | MDA-MB-231 | LC50 | 1.7 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | MDA-MB-231 | LC50 | 64.3 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | MDA-MB-231 | TGI | 1.01 | nM | 10.1016/j.bmc.2010.07.049 |
| Homo sapiens | MDA-MB-231 | TGI | 57.8 | nM | 10.1016/j.bmc.2008.07.083 |
| Homo sapiens | P-glycoprotein 1 | FC | 16.0 | None | 10.1016/j.ejmech.2017.06.047 |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 3.3 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 4.3 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 6.7 | nM | None |
| Mus musculus | B16 | T/C | 241.0 | % | 10.1021/np50117a002 |
| Mus musculus | L1210 | IC50 | 0.0005 | ug.mL-1 | 10.1021/np50070a001 |
| Mus musculus | M5076 | T/C | 210.0 | % | 10.1021/np50117a002 |
| Mus musculus | P388 | T/C | 167.0 | % | 10.1021/np50070a001 |
| Mus musculus | P388 | T/C | 213.0 | % | 10.1021/np50117a002 |
| None | ADMET | Activity | 1.0 | None | 10.1073/pnas.0609877104 |
| None | ADMET | CL | 12.0 | mL.min-1.kg-1 | 10.1124/dmd.108.020479 |
| None | ADMET | GI50 | 46.0 | nM | 10.1016/j.bmc.2006.10.009 |
| None | ADMET | IC50 | 6.0 | nM | 10.1073/pnas.0609877104 |
| None | ADMET | MRT | 35.0 | hr | 10.1124/dmd.108.020479 |
| None | ADMET | T1/2 | 44.0 | hr | 10.1124/dmd.108.020479 |
| None | ADMET | Vdss | 25.0 | L.kg-1 | 10.1124/dmd.108.020479 |
| None | Hepatotoxicity | Hepatotoxicity | nan | None | 10.1021/tx900326k |
| None | Lymphocyte | Activity | nan | None | 10.1073/pnas.0609877104 |
| None | NON-PROTEIN TARGET | Fold change | 8.0 | None | 10.1073/pnas.0609877104 |
| None | NON-PROTEIN TARGET | Fold change | 18.0 | None | 10.1073/pnas.0609877104 |
| None | NON-PROTEIN TARGET | Fold change | 23.0 | None | 10.1073/pnas.0609877104 |
| None | NON-PROTEIN TARGET | T/C | 0.0 | % | 10.1021/np50117a002 |
| None | Unchecked | Activity | 1.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 2.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 3.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 14.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 19.0 | % | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 35.0 | % | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 42.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 65.0 | % | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 90.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Activity | 100.0 | None | 10.1073/pnas.0609877104 |
| None | Unchecked | Potency | 2818.4 | nM | None |
| None | Unchecked | Potency | 28183.8 | nM | None |
| None | Unchecked | Potency | 39810.7 | nM | None |
| None | Unchecked | Potency | 100000.0 | nM | None |