paclitaxel (Q423762)

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chemical compound
  • BMS-181339-01
  • PAX
  • taxol
  • 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
  • taxol A
edit
Language Label Description Also known as
English
paclitaxel
chemical compound
  • BMS-181339-01
  • PAX
  • taxol
  • 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
  • taxol A

Statements

mass
853.331 dalton
1 reference
stated in
PubChem
PubChem CID
36314
language of work or name
English
title
paclitaxel (English)
retrieved
18 November 2016
chemical formula
C₄₇H₅₁NO₁₄
1 reference
stated in
PubChem
PubChem CID
36314
language of work or name
English
title
paclitaxel (English)
retrieved
18 November 2016
canonical SMILES
CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
1 reference
stated in
PubChem
PubChem CID
36314
language of work or name
English
title
paclitaxel (English)
retrieved
18 November 2016
isomeric SMILES
CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
1 reference
stated in
PubChem
PubChem CID
36314
language of work or name
English
title
paclitaxel (English)
retrieved
18 November 2016
found in taxon
Taxus brevifolia
34 references
stated in
A Brief Survey of Taxus Alkaloids and Other Taxane Derivatives
stated in
Biosynthesis of Taxol
stated in
Concentrations of taxol and related taxanes in the needles of differentTaxus cultivars
stated in
Purification and characterization of taxa-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis
stated in
Heterologous expression and characterization of a "Pseudomature" form of taxadiene synthase involved in paclitaxel (Taxol) biosynthesis and evaluation of a potential intermediate and inhibitors of the multistep diterpene cyclization reaction
stated in
Embryo culture and taxane production inTaxus spp
stated in
Free taxanes and the release of bound compounds having taxane antibody reactivity by xylanase in female, haploid-derived cell suspension cultures ofTaxus brevifolia
stated in
Determination of taxol in Taxus species grown in Hungary by high-performance liquid chromatography-diode array detection effect of vegetative period
stated in
Taxol content in the seeds of Taxus SPP
stated in
Taxol partitioning in two-phase plant cell cultures of Taxus brevifolia
stated in
Taxol formation in yew — Taxus
stated in
Supercritical extraction of taxol from the bark of Taxus brevifolia
stated in
Rapid screening for taxanes by tandem mass spectrometry
stated in
High-performance liquid chromatographic assay of taxol
stated in
Mechanism of taxadiene synthase, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in Pacific yew
stated in
Biosynthesis of taxoids. Mode of formation of the taxol side chain
stated in
New taxanes from Taxus brevifolia
stated in
Taxus spp. needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation
stated in
Taxol content in bark, wood, root, leaf, twig, and seedling from several Taxus species
stated in
Effects of genetic, epigenetic, and environmental factors on taxol content in Taxus brevifolia and related species
stated in
Taxol and Cephalomannine Concentrations in the Foliage and Bark of Shade-Grown and Sun-Exposed Taxus brevifolia Trees
stated in
Determination of Taxanes in Taxus brevifolia Extracts by Tandem Mass Spectrometry and High-Performance Liquid Chromatography
stated in
Brevitaxin, a new diterpenolignan from the bark of Taxus brevifolia
stated in
Taxol and taxane formation in plant cell culture
stated in
Neutral and basic taxoid contents in the needles of Taxus species
stated in
Taxol Biosynthesis: An Update
stated in
Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the committed step of taxol biosynthesis in Pacific yew
stated in
A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis
stated in
HPLC Separation of Taxol and Cephalomannine
stated in
Methodology for the Identification and Purification of Taxol and Cephalomannine from Taxus Callus Cultures
stated in
EFFICIENT EXTRACTION OF PACLITAXEL AND RELATED TAXOIDS FROM LEAF TISSUE OF TAXUS USING A POTABLE SOLVENT SYSTEM
stated in
Biosynthetic studies on taxol
stated in
Biosynthetic Studies on Taxol
stated in
Biosynthesis of Taxol
Taxus canadensis
17 references
stated in
Determination of taxane concentrations in Taxus canadensis clippings using high performance liquid chromatographic analysis with an internal standard
stated in
Analysis of taxol and related taxanes fromtaxus canadensis using liquid chromatography combined with mass spectrometry or tandem mass spectrometry
stated in
Taxol production and taxadiene synthase activity in Taxus canadensis cell suspension cultures
stated in
Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis
stated in
Preparative separation of taxol in normal- and reversed-phase operations
stated in
Taxol content of various Taxus species in Hungary
stated in
Two new taxanes from Taxus canadensis
stated in
Biosynthetic building blocks of taxanes
stated in
Challenges in the isolation of taxanes from Taxus canadensis by fast pyrolysis
stated in
Oligosaccharides potentiate methyl jasmonate-induced production of paclitaxel in Taxus canadensis
stated in
Rapid screening for taxanes by tandem mass spectrometry
stated in
Taxus spp. needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation
stated in
Isolation of 9-Dihydro-13-acetylbaccatin III from Taxus canadensis
stated in
Isolation of labeled 9-dihydrobaccatin III and related taxoids from cell cultures of taxuscell cultures of taxus canadensis elicited with m
stated in
Neutral and basic taxoid contents in the needles of Taxus species
stated in
Yew (taxus) species - chemical and morphological variations
stated in
Seasonal Changes in the Concentration of Major Taxanes in the Biomass of Wild Canada Yew (Taxus canadensis. Marsh.)
Taxus baccata
41 references
stated in
Methodology for the Identification and Purification of Taxol and Cephalomannine from Taxus Callus Cultures
stated in
Immunoenzymatic methods applied to the search for bioactive taxoids from Taxus baccata
stated in
Taxol on the surface of leaves and inside the needles of three species and two varieties of Taxus
stated in
Sample preparation for taxol and cephalomannine determination in various organs of Taxus sp
stated in
Analysis of taxol, 10-deacetylbaccatin III and related compounds in Taxus baccata
stated in
Taxol production in suspension cultures of Taxus baccata
stated in
Production of taxanes by Taxus baccata plant cells
stated in
Taxol content of Irish yews
stated in
Seasonal changes in the concentrations of four taxoids in Taxus baccata L. during the autumn-spring period
stated in
Seasonal variations in the content of taxanes in the bark of Taxus baccata L.
stated in
INVESTIGATIONS ON PREPARATIVE THIN-LAYER CHROMATOGRAPHIC SEPARATION OF TAXOIDS FROM TAXUS BACCATA L.
stated in
Concentrations of taxol and related taxanes in the needles of differentTaxus cultivars
stated in
Screening for pharmaceutically important taxoids in Taxus baccata var. Aurea corr. with CC/SPE/HPLC-PDA procedure
stated in
Yew (taxus) species - chemical and morphological variations
stated in
Neutral and basic taxoid contents in the needles of Taxus species
stated in
Seasonal variation of neutral and basic taxoid contents in shoots of European Yew (Taxus baccata)
stated in
Taxol content in the bark of Himalayan Yew in relation to tree age and sex.
stated in
Taxanes in Taxus baccata pollen: cardiotoxicity and/or allergenicity?
stated in
Taxus spp. needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation
stated in
Taxol content in bark, wood, root, leaf, twig, and seedling from several Taxus species
stated in
Effects of genetic, epigenetic, and environmental factors on taxol content in Taxus brevifolia and related species
stated in
Relationships between the structures of taxol and baccatine III derivatives and their in vitro action on the disassembly of mammalian brain and Physarum amoebal microtubules
stated in
New bioactive taxoids from cell cultures of Taxus baccata
stated in
Taxanes from Taxus baccata
stated in
A yew in Israel, new taxane derivatives
stated in
Taxol content in the seeds of Taxus SPP
stated in
Taxol content of various Taxus species in Hungary
stated in
Taxol content in the storage samples of the needles of Himalayan Taxus baccata and their extracts
stated in
Application of supercritical fluid extraction and supercritical fluid chromatography to the production of taxanes as anti-cancer drugs
stated in
Production of Taxol® and baccatin III by a selected Taxus baccata callus line and its derived cell suspension culture
stated in
Antimicrobial activity of the heartwood of Taxus baccata
stated in
Method of isolating taxol from Taxus baccata
stated in
High-Speed Countercurrent Chromatography Separation of Taxol and Related Diterpenoids fromTaxus Baccata
stated in
Rapid screening for taxanes by tandem mass spectrometry
stated in
Determination of paclitaxel and related diterpenoids in plant extracts by high-performance liquid chromatography with UV detection in high-performance liquid chromatography–mass spectrometry
stated in
Taxol production in bioreactors: Kinetics of biomass accumulation, nutrient uptake, and taxol production by cell suspensions of Taxus baccata
stated in
Induction of geranylgeranyl diphosphate synthase activity and taxane accumulation in Taxus baccata cell cultures after elicitation by methyl jasmonate
stated in
Geranylgeranyl diphosphate synthase activity and taxane production in Taxus baccata cells
stated in
Taxol transport in Taxus baccata cell suspension cultures
stated in
A Yew in Israel, New Taxane Derivatives
stated in
Production of Taxanes in a Bioreactor by Taxus baccata Cells
Taxus wallichiana
24 references
stated in
Novel taxane diterpenes from Taxus sumatrana with the first C-21 taxane ester
stated in
Taxol and its related taxoids from the needles of Taxus sumatrana.
stated in
Chemical Study of Indonesian Medicinal Plants
stated in
Novel Taxane Diterpenes from Taxus sumatrana with the First C-21 Taxane Ester
stated in
High Performance Liquid Chromatographic Determination of Taxol and Related Taxanes from Taxus Callus Cultures
stated in
Improved taxol yield in cell suspension culture of Taxus wallichiana (Himalayan yew)
stated in
Semi-preparative separation and purification of taxol analogs by high-speed countercurrent chromatography
stated in
Analysis of taxol and major taxoids in Himalayan yew, Taxus wallichiana
stated in
Variation in content of taxol and related taxanes in Eastern Himalayan populations of Taxus wallichiana
stated in
Taxol Related Diterpenes from the Roots of Taxus yunnanensis
stated in
Wallifoliol, a taxol congener with a novel carbon skeleton, from Himalayan Taxus wallichiana
stated in
Taxoids from the barks of Taxus wallichiana
stated in
A New Taxane Diterpene fromTaxus yunnanensis
stated in
New taxane diterpenoids from the leaves and twigs of Taxus sumatrana
stated in
Diterpenes and sesquiterpenes from the bark of Taxus yunnanensis
stated in
New Taxane Diterpenoids from Taxus yunnanensis
stated in
Chemical constituents of Taxus species
stated in
The taxoid constituents of the roots of Taxus wallichiana
stated in
Production of Paclitaxel and Baccatin III in a 20-L Airlift Bioreactor by a Cell Suspension of Taxus wallichiana
stated in
LARGE-SCALE PROCESS FOR HIGH PURITY TAXOL FROM BARK EXTRACT OFTAXUS YUNNANESIS
stated in
A Large Scale Separation of Taxanes from the Bark Extract of Taxus yunnanesis and 1H- and 13C-NMR Assignments for 7-epi-10-Deacetyltaxol
stated in
Stimulation of taxol production and excretion in Taxus spp cell cultures by rare earth chemical lanthanum
stated in
High Performance Liquid Chromatographic Determination of Taxol and Related Taxanes from Texas Callus Cultures
stated in
Constituents from Taxus species
Taxus cuspidata
49 references
stated in
Methodology for the Identification and Purification of Taxol and Cephalomannine from Taxus Callus Cultures
stated in
Taxol on the surface of leaves and inside the needles of three species and two varieties of Taxus
stated in
Microwave-Assisted Extraction of Taxanes fromTaxusBiomass
stated in
Sample preparation for taxol and cephalomannine determination in various organs of Taxus sp
stated in
High Performance Liquid Chromatographic Determination of Taxol and Related Taxanes from Taxus Callus Cultures
stated in
Taxol production in suspension cultures of Taxus baccata
stated in
Distribution and amounts of taxol in different shoot parts of Taxus cuspidata
stated in
Qualitative and quantitative determination of taxol and related compounds inTaxus cuspidata Sieb et Zucc
stated in
Roots of hydroponically grown Taxus plants as a source of taxol and related taxanes
stated in
Taxol and related compounds in Korean native yews (Taxus cuspidata)
stated in
Continuous production of taxol by cell culture of taxus cuspidata.
stated in
Recycling High-Speed Countercurrent Chromatography for Separation of Taxol and Cephalomannine
stated in
Concentrations of taxol and related taxanes in the needles of differentTaxus cultivars
stated in
Studies on factors influencing stability and recovery of paclitaxel from suspension media and cultures of Taxus cuspidata cv Densiformis by high-performance liquid chromatography
stated in
Yew (taxus) species - chemical and morphological variations
stated in
Neutral and basic taxoid contents in the needles of Taxus species
stated in
Efficient Paclitaxel Production using Protoplasts Isolated from Cultured Cells of Taxus cuspidata
stated in
Taxus spp. needles contain amounts of taxol comparable to the bark of Taxus brevifolia: analysis and isolation
stated in
Taxol content in bark, wood, root, leaf, twig, and seedling from several Taxus species
stated in
Determination of taxol by high-performance liquid chromatography-thermospray mass spectrometry
stated in
Effects of genetic, epigenetic, and environmental factors on taxol content in Taxus brevifolia and related species
stated in
Taxuspines A ∼ C, new taxoids from Japanese yew Taxus cuspidata inhibiting drug transport activity of P-glycoprotein in multidrug-resistant cells
stated in
Taxuspines E ∼ H and J, new taxoids from the Japanese yew Taxus cuspidata
stated in
A taxoid from Taxus cuspidata var. nana
stated in
A taxoid from the needles of the Japanese yew, Taxus cuspidata
stated in
A Novel Rearranged Taxoid from Needles of the Japanese Yew, Taxus cuspidata Sieb. et Zucc
stated in
Taxol content in the seeds of Taxus SPP
stated in
Effects of taxoids from Taxus cuspidata on microtubule depolymerization and vincristine accumulation in MDR cells
stated in
Supercritical fluid extraction of paclitaxel and baccatin III from needles of taxus cuspidata
stated in
Taxol content of various Taxus species in Hungary
stated in
Taxol (paclitaxel) production using free and immobilized cells of Taxus cuspidata
stated in
Accelerated solvent extraction of paclitaxel and related compounds from the bark of taxus cuspidata
stated in
A Novel Method of Isolating Taxanes from Cell Suspension Cultures of Yew (TaxusSpp.)
stated in
Taxol
stated in
Supercritical fluid extraction of taxol and baccatin III from needles of Taxus cuspidata
stated in
RECOVERY OF TAXOL FROM THE EXTRACT OF TAXUS CUSPIDATE CALLUS CULTURES WITH AL2O3 CHROMATOGRAPHY
stated in
Kinetics of two-liquid-phase Taxus cuspidata cell culture for production of Taxol
stated in
Purification of S-PG05 using Simulated Moving Bed Chromatography
stated in
Large-scale growth and taxane production in cell cultures of Taxus cuspidata (Japanese yew) using a novel bioreactor
stated in
Immunocytochemical Localization of Taxol in Taxus cuspidata
stated in
Rapid screening for taxanes by tandem mass spectrometry
stated in
Improved growth and taxol yield in developing calli of Taxus cuspidata by medium composition modification.
stated in
Influence of water extracts from the surface of two yew (Taxus) species on mites (Tetranychus urticae)
stated in
Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis
stated in
Taxol biosynthesis: differential transformations of taxadien-5 alpha-ol and its acetate ester by cytochrome P450 hydroxylases from Taxus suspension cells
stated in
Taxol biosynthesis: taxane 13 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase
stated in
Taxol biosynthesis: molecular cloning of a benzoyl-CoA:taxane 2alpha-O-benzoyltransferase cDNA from taxus and functional expression in Escherichia coli
stated in
High Performance Liquid Chromatographic Determination of Taxol and Related Taxanes from Texas Callus Cultures
stated in
Taxol production in nodule cultures of Taxus
legal status (medicine)
boxed warning
1 reference
reference URL
https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
title
FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links. (English)
Commons category
Paclitaxel
0 references

Identifiers

CAMEO Chemicals ID
21061
0 references
HSDB ID
6839
1 reference
stated in
Hazardous Substances Data Bank
HSDB ID
6839
publication date
28 October 2019
title
TAXOL (English)
retrieved
10 May 2021
LiverTox ID
Paclitaxel
0 references
NSC number
125973
0 references
758645
0 references
EC number
608-826-9
1 reference
stated in
ECHA Substance Infocard database
ECHA Substance Infocard ID
100.127.725
retrieved
27 December 2018
title
(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro-4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate, 12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine (English)
quotation
CAS no.: 33069-62-4 (English)
ECHA Substance Infocard ID
100.127.725
1 reference
stated in
ECHA Substance Infocard database
ECHA Substance Infocard ID
100.127.725
retrieved
27 December 2018
title
(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro-4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate, 12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine (English)
quotation
CAS no.: 33069-62-4 (English)
MeSH descriptor ID
D017239
subject named as
Paclitaxel
0 references
PDB ligand ID
TA1
0 references
CAB ID
18845
1 reference
stated in
CAB Thesaurus
retrieved
6 April 2020
DeCS ID
30485
0 references
NALT ID
34126
0 references
PDB structure ID
UNSPSC Code
51111904
0 references
 
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