CHEBI:45863 - paclitaxel

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ChEBI Name paclitaxel
ChEBI ID CHEBI:45863
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7887, CHEBI:45862
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Formula C47H51NO14
Net Charge 0
Average Mass 853.90618
Monoisotopic Mass 853.331
InChI InChI=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
InChIKey RCINICONZNJXQF-MZXODVADSA-N
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@@]21OC(C)=O)C3(C)C
Metabolite of Species Details
Taxomyces andreanae (NCBI:1117664) An endophytic fungus living within the inner tissues of Taxus brevifolia See: PubMed
Paraconiothyrium (NCBI:300251) An endophytic fungus in branches of Taxus media plants of strain SSM001 See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
microtubule-stabilising agent
Any substance that interacts with tubulin to promote polymerisation of microtubules.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 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 Sources
(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 ester ChemIDplus
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-phenylisoserine ChemIDplus
Paclitaxel KEGG COMPOUND
TAXOL PDBeChem
taxol UniProt
Taxol A ChemIDplus
Database Links Databases
2044 DrugCentral
C00002365 KNApSAcK
C07394 KEGG COMPOUND
D00491 KEGG DRUG
DB01229 DrugBank
Paclitaxel Wikipedia
TA1 PDBeChem
View more database links
Registry Number Type Source
33069-62-4 CAS Registry Number ChemIDplus
Last Modified
22 February 2017