CHEBI:45863 - paclitaxel

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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:CB8194893, ChemicalBook:CB3512063, eMolecules:485716, eMolecules:6760397, ZINC000003831417
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Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement. Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development. Dietary sources include fish, dairy products, and meat. As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia. It is taken by mouth or by injection into a muscle. As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging. Retinol at normal doses is well tolerated. High doses may cause enlargement of the liver, dry skin, and hypervitaminosis A. High doses during pregnancy may harm the fetus. The body converts retinol to retinal and retinoic acid, through which it acts. Retinol was discovered in 1909, isolated in 1931, and first made in 1947. It is on the World Health Organization's List of Essential Medicines. Retinol is available as a generic medication and over the counter. In 2021, vitamin A was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.
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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