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
Supplier Information ChemicalBook:CB6851738
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Wikipedia License
Ozone () (or trioxygen) is an inorganic molecule with the chemical formula O3. It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope O2, breaking down in the lower atmosphere to O2 (dioxygen). Ozone is formed from dioxygen by the action of ultraviolet (UV) light and electrical discharges within the Earth's atmosphere. It is present in very low concentrations throughout the atmosphere, with its highest concentration high in the ozone layer of the stratosphere, which absorbs most of the Sun's ultraviolet (UV) radiation. Ozone's odor is reminiscent of chlorine, and detectable by many people at concentrations of as little as 0.1 ppm in air. Ozone's O3 structure was determined in 1865. The molecule was later proven to have a bent structure and to be weakly diamagnetic. At standard temperature and pressure, ozone is a pale blue gas that condenses at cryogenic temperatures to a dark blue liquid and finally a violet-black solid. Ozone's instability with regard to more common dioxygen is such that both concentrated gas and liquid ozone may decompose explosively at elevated temperatures, physical shock, or fast warming to the boiling point. It is therefore used commercially only in low concentrations. Ozone is a powerful oxidizing agent (far more so than dioxygen) and has many industrial and consumer applications related to oxidation. This same high oxidizing potential, however, causes ozone to damage mucous and respiratory tissues in animals, and also tissues in plants, above concentrations of about 0.1 ppm. While this makes ozone a potent respiratory hazard and pollutant near ground level, a higher concentration in the ozone layer (from two to eight ppm) is beneficial, preventing damaging UV light from reaching the Earth's surface.
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Formula C47H51NO14
Net Charge 0
Average Mass 853.90618
Monoisotopic Mass 853.33096
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:txid1117664) An endophytic fungus living within the inner tissues of Taxus brevifolia See: PubMed
Paraconiothyrium (NCBI:txid300251) An endophytic fungus in branches of Taxus media plants of strain SSM001 See: PubMed
Homo sapiens (NCBI:txid9606) 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
paclitaxel UniProt
TAXOL PDBeChem
Taxol A ChemIDplus
Manual Xrefs 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
12 June 2024