CHEBI:4672 - docetaxel anhydrous

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ChEBI Name docetaxel anhydrous
ChEBI ID CHEBI:4672
Definition A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C43H53NO14
Net Charge 0
Average Mass 807.87920
Monoisotopic Mass 807.34661
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
InChIKey ZDZOTLJHXYCWBA-VCVYQWHSSA-N
SMILES [H][C@@]1(C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@]3([H])[C@@]4(CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C(=C1C)C2(C)C)OC(C)=O)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c1ccccc1
Roles Classification
Biological Role(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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ChEBI Ontology
Outgoing docetaxel anhydrous (CHEBI:4672) has parent hydride taxane (CHEBI:36064)
docetaxel anhydrous (CHEBI:4672) has role antimalarial (CHEBI:38068)
docetaxel anhydrous (CHEBI:4672) has role antineoplastic agent (CHEBI:35610)
docetaxel anhydrous (CHEBI:4672) has role photosensitizing agent (CHEBI:47868)
docetaxel anhydrous (CHEBI:4672) is a secondary α-hydroxy ketone (CHEBI:2468)
docetaxel anhydrous (CHEBI:4672) is a tetracyclic diterpenoid (CHEBI:52557)
Incoming docetaxel trihydrate (CHEBI:59809) has part docetaxel anhydrous (CHEBI:4672)
IUPAC Name
4-(acetyloxy)-13α-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7β,10β-trihydroxy-9-oxo-5β,20-epoxytax-11-en-2α-yl benzoate
Synonyms Sources
Docetaxel KEGG COMPOUND
Docetaxel anhydrous KEGG COMPOUND
N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel ChEBI
N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol ChEBI
TXL DrugBank
Manual Xrefs Databases
C11231 KEGG COMPOUND
D07866 KEGG DRUG
DB01248 DrugBank
Docetaxel Wikipedia
EP253738 Patent
TXL PDBeChem
US4814470 Patent
View more database links
Registry Numbers Types Sources
114977-28-5 CAS Registry Number KEGG COMPOUND
114977-28-5 CAS Registry Number ChemIDplus
4290183 Beilstein Registry Number Beilstein
Last Modified
06 February 2018
General Comment
2011-03-18 Docetaxel is prepared from a natural precursor, 10-deacetylbaccatin III, extracted fron the needles of the European yew tree, Taxus baccata. It is used (often as the trihydrate) for the treatment of breast, ovarian, and non-small cell lung cancer, and with prednisone or prednisolone in hormone-refractory metastatic prostate cancer.