Responsive image

Common name


Docetaxel

IUPAC name


(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹

SMILES


[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1

Compound class


Antineoplastic Agents; Immunosuppressive Agents; Tubulin Modulators; Antineoplastic and Immunomodulating Agents; Taxanes; CYP3A4 Inhibitors;

Therapeutic area


For the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Also used as a single agent in the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. It is also used in combination with prednisone, in the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. Furthermore, docetaxel has uses in the treatment of gastric adenocarinoma and head and neck cancer.

Common name


Docetaxel

IUPAC name


(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹

SMILES


[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1

INCHI


InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1

FORMULA


C43H53NO14

Responsive image

Common name


Docetaxel

IUPAC name


(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹

Molecular weight


807.879

clogP


3.512

clogS


-5.148

HBond Acceptor


14

HBond Donor


5

Total Polar
Surface Area


224.45

Number of Rings


6

Rotatable Bond


13

Drug ID Common name Structure CAS SMILE Frequency
FDBF00004 acetic acid Responsive image CC(=O)O 0.0687
FDBF00005 benzene Responsive image c1ccccc1 0.2824
FDBF00012 isobutane Responsive image C(C)(C)C 0.0611
FDBF00023 toluene Responsive image c1(ccccc1)C 0.1268
FDBF00041 ethanol Responsive image CCO 0.1474
FDBF00253 2-phenylethanol Responsive image c1(ccccc1)CCO 0.0038
FDBF01127 methylcarbamic acid Responsive image O=C(O)NC 0.0199
FDBF02839 tert-butyl carbamate Responsive image O(C(=O)N)C(C)(C)C 0.0010
FDBF02840 benzylcarbamic acid Responsive image O=C(O)NCc1ccccc1 0.0003
FDBF02841 tert-butyl N-methylcarbamate Responsive image O(C(=O)NC)C(C)(C)C 0.0003
10 , 2