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CHEBI:45863 - paclitaxel

Default Structure
ChEBI IDCHEBI:45863
ChEBI Namepaclitaxel
Stars
DefinitionA tetracyclic diterpenoid isolated originally from the bark of the Pacific yew tree, Taxus brevifolia. It is a mitotic inhibitor used in cancer chemotherapy. Note that the use of the former generic name 'taxol' is now limited, as Taxol is a registered trade mark.
Secondary ChEBI IDsCHEBI:7887, CHEBI:45862
Last Modified12 June 2024
DownloadsMolfile
FormulaC47H51NO14
Net Charge0
Average Mass853.918
Monoisotopic Mass853.33096
SMILES[H][C@]12[C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C([C@@H](OC(C)=O)C(=O)[C@]1(C)[C@@H](O)C[C@H]1OC[C@]12OC(C)=O)C3(C)C
InChIInChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChIKeyRCINICONZNJXQF-MZXODVADSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Paraconiothyrium (ncbitaxon:300251) - PubMed (22103292) An endophytic fungus in branches of Taxus media plants Strain: SSM001
Taxomyces andreanae (ncbitaxon:1117664) - PubMed (22103292) An endophytic fungus living within the inner tissues of Taxus brevifolia
Roles Classification
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
microtubule-stabilising agent  Any substance that interacts with tubulin to promote polymerisation of microtubules.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
paclitaxel (CHEBI:45863) has functional parent baccatin III (CHEBI:32898)
paclitaxel (CHEBI:45863) has role antineoplastic agent (CHEBI:35610)
paclitaxel (CHEBI:45863) has role human metabolite (CHEBI:77746)
paclitaxel (CHEBI:45863) has role metabolite (CHEBI:25212)
paclitaxel (CHEBI:45863) has role microtubule-stabilising agent (CHEBI:61950)
paclitaxel (CHEBI:45863) is a taxane diterpenoid (CHEBI:50367)
paclitaxel (CHEBI:45863) is a tetracyclic diterpenoid (CHEBI:52557)
Incoming Relation(s)
6-hydroxypaclitaxel (CHEBI:63859) has functional parent paclitaxel (CHEBI:45863)
IUPAC Name 
4α,10β-bis(acetyloxy)-13α-[(2S,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy]-1,7β-dihydroxy-9-oxo-5β,20-epoxytax-11-en-2α-yl benzoate
Synonyms  Source
(2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alpha R*,betaS*),11alpha,12alpha,12balpha))-beta-(Benzoylamino)-alpha-hydroxybenzenepropanoic acid 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl esterChemIDplus
5beta,20-Epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserineChemIDplus
PaclitaxelKEGG COMPOUND
TAXOLPDBeChem
Taxol AChemIDplus
UniProt Name  Source
paclitaxelUniProt
Manual XrefsDatabases
2044DrugCentral
C00002365KNApSAcK
C07394KEGG COMPOUND
D00491KEGG DRUG
DB01229DrugBank
PaclitaxelWikipedia
TA1PDBeChem
Registry NumbersSources
CAS:33069-62-4KEGG COMPOUND
CAS:33069-62-4ChemIDplus