(1R,12S,14R)-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(9),5,7,15,20,22-hexaen-22-yl acetate

• ChemBase ID: 178791
• Molecular Formular: C39H43N3O11S
• Molecular Mass: 761.83722
• Monoisotopic Mass: 761.26183021
• SMILES: c1(c2c(c3c(c1OC(=O)C)[C@@H]1C4N([C@H]3COC(=O)C3(c5c(CCN3)cc(c(c5)OC)O)CS1)[C@H](C1N(C4c3c(C1)cc(c(c3O)OC)C)C)O)OCO2)C
• Canonical SMILES: COc1cc2c(cc1O)CCNC12CS[C@@H]2c3c(OC(=O)C)c(C)c4c(c3[C@H](COC1=O)N1C2C2N(C([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
• InChIKey: PKVRCIRHQMSYJX-XHNODKIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,12S,14R)-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[12.9.6.1^3,^1^1.0^2,^1^3.0^4,^9.0^1^5,^2^3.0^1^6,^2^0]triacontane-26,1'-isoquinoline]-4(9),5,7,15,20,22-hexaen-22-yl acetate
• IUPAC Traditional name: (1R,12S,14R)-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[12.9.6.1^3,^1^1.0^2,^1^3.0^4,^9.0^1^5,^2^3.0^1^6,^2^0]triacontane-26,1'-isoquinoline]-4(9),5,7,15,20,22-hexaen-22-yl acetate
• Synonyms: (1'R,6R,6aR,7R,13S,14S,16R)-5-(Acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethylspiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinolin]-19-one; Ecteinascidin 743; Et 743; NSC 648766; Yondelis; Trabectedin

Database IDs

• CAS Number: 114899-77-3
• PubChem SID: 164234701
• PubChem CID: 71752642

CALCULATED PROPERTIES

• Acid pKa: 9.27128
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 1.8768625
• LogD (pH = 7.4): 3.7126172
• Log P: 3.9873106
• Molar Refractivity: 196.921 cm^3
• Polarizability: 77.282715 Å^3
• Polar Surface Area: 168.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T703500

A tetrahydroisoquinoline alkaloid with antitumor activity isolated from the Caribbean tunicate, Ecteinascidin turbinata. It is the first marine anticancer agent approved in the European Union for patients with soft tissue sarcoma (STS). Antineoplastic.

REFERENCES

• Sakai, R., et al.: Proc. Natl. Acad. Sci., 89, 11456 (1992)
• Aune, G., et al.: Anticancer Drugs, 13, 545 (1992)
• Herrero, A., et al.: Cancer Res., 66, 8155 (1992)
• Sugasawa, K., et al.: Carcinogenesis, 29, 455 (1992)