Trabectedin (CHEM019326)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:01:39 UTC
Update Date2026-04-14 15:33:43 UTC
Accession NumberCHEM019326
Identification
Common NameTrabectedin
ClassSmall Molecule
DescriptionTrabectedin, also referred as Trabectedin during its development, is a marine-derived antitumor agent discovered in the Carribean tunicate _Ecteinascidia turbinata_ and now produced synthetically. Trabectedin has a unique mechanism of action. It binds to the minor groove of DNA interfering with cell division and genetic transcription processes and DNA repair machinery. It is approved for use in Europe, Russia and South Korea for the treatment of advanced soft tissue sarcoma. It is currently under evaluation for the treatment of breast cancer, prostate cancer, in addition to pediatric sarcomas. Both the European Commission and the U.S. Food and Drug Administration (FDA) have approved trabectedin as an orphan drug in soft tissue sarcomas and ovarian cancer. On October 23, 2015, the FDA approved trabectedin, (as Yondelis), for the treatment of specific soft tissue sarcomas.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ect 743ChEBI
EcteinascidinChEBI
Ecteinascidin 743ChEBI
ET-743ChEBI
ET743ChEBI
YondelisChEBI
NSC 684766HMDB
Chemical FormulaC39H43N3O11S
Average Molecular Mass761.837 g/mol
Monoisotopic Mass761.262 g/mol
CAS Registry Number114899-77-3
IUPAC Name(1R,2R,3R,11S,12S,14R,26R)-5,6',12-trihydroxy-6,7'-dimethoxy-7,21,30-trimethyl-27-oxo-3',4'-dihydro-2'H-17,19,28-trioxa-24-thia-13,30-diazaspiro[heptacyclo[12.9.6.1³,¹¹.0²,¹³.0⁴,⁹.0¹⁵,²³.0¹⁶,²⁰]triacontane-26,1'-isoquinoline]-4,6,8,15,20,22-hexaen-22-yl acetate
Traditional Nameyondelis
SMILES[H][C@@]12[C@@H]3SC[C@]4(NCCC5=C4C=C(OC)C(O)=C5)C(=O)OC[C@H](N1[C@@H](O)[C@@H]1CC4=CC(C)=C(OC)C(O)=C4[C@H]2N1C)C1=C2OCOC2=C(C)C(OC(C)=O)=C31
InChI IdentifierInChI=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 KeyPKVRCIRHQMSYJX-AIFWHQITSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzazocines. These are organic compounds containing the benzazocine ring system, which consists of a benzene ring bound to an azocine ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzazocines
Direct ParentBenzazocines
Alternative Parents
Substituents
  • Benzazocine
  • Tetrahydroisoquinoline
  • Alpha-amino acid or derivatives
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • N-methylpiperazine
  • N-alkylpiperazine
  • Aralkylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Piperazine
  • 1,4-diazinane
  • Hemiaminal
  • Lactone
  • Tertiary aliphatic amine
  • Carboxylic acid ester
  • Tertiary amine
  • Amino acid or derivatives
  • Acetal
  • Alkanolamine
  • Carboxylic acid derivative
  • Oxacycle
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkylthioether
  • Thioether
  • Polyol
  • Secondary amine
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.04ALOGPS
logP3.99ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)7.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area168.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity196.92 m³·mol⁻¹ChemAxon
Polarizability77.72 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgr-0090000100-1fbe6c879e491f9c397cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-e91cca9b4689a68d194cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0300002900-083c4ab0de6a8cbf080dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-2130029700-488b00bc8602ecbb0612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-5dd80d9620ee90346daaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-11ou-1000001900-ea86efb65818a8f27be5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kac-6050009800-1902e4760cf83e432109Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-cf19b0cf6f95b02564a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000900-3e1fdba9b1bd766aa3dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vl-0010008900-6487d80738403778f792Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-2edcd395ca8015613eaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000900-2874db466c2b035d495bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tl-0200016900-85e72ee9c89dddad28e0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB05109
HMDB IDHMDB0015609
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDECT
Wikipedia LinkTrabectedin
Chemspider ID97236
ChEBI ID84050
PubChem Compound ID108150
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Authors unspecified: Trabectedin: Ecteinascidin 743, Ecteinascidin-743, ET 743, ET-743, NSC 684766. Drugs R D. 2006;7(5):317-28.
2. Carter NJ, Keam SJ: Trabectedin : a review of its use in the management of soft tissue sarcoma and ovarian cancer. Drugs. 2007;67(15):2257-76.
3. Krasner CN, McMeekin DS, Chan S, Braly PS, Renshaw FG, Kaye S, Provencher DM, Campos S, Gore ME: A Phase II study of trabectedin single agent in patients with recurrent ovarian cancer previously treated with platinum-based regimens. Br J Cancer. 2007 Dec 17;97(12):1618-24. Epub 2007 Nov 13.
4. Tavecchio M, Natoli C, Ubezio P, Erba E, D'Incalci M: Dynamics of cell cycle phase perturbations by trabectedin (ET-743) in nucleotide excision repair (NER)-deficient and NER-proficient cells, unravelled by a novel mathematical simulation approach. Cell Prolif. 2007 Dec;40(6):885-904.
5. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1.
6. Guirouilh-Barbat J, Antony S, Pommier Y: Zalypsis (PM00104) is a potent inducer of gamma-H2AX foci and reveals the importance of the C ring of trabectedin for transcription-coupled repair inhibition. Mol Cancer Ther. 2009 Jul;8(7):2007-14. doi: 10.1158/1535-7163.MCT-09-0336. Epub 2009 Jul 7.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21403840
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21499557
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23149213
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24001124
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24277455
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24662672
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24692579
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24696229
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24707261
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24755886
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24756367
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24803896
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24844217
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24917554
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24941346
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24982387
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=25048043
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=25048044
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=25050069
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=25076252
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=25100135
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=25209722
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=25263179
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=25273374
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=25479910