ChemSpider 2D Image | Docetaxel | C43H53NO14

Docetaxel

  • Molecular FormulaC43H53NO14
  • Average mass807.879 Da
  • Monoisotopic mass807.346619 Da
  • ChemSpider ID130581

  • defined stereocentres - 11 of 11 defined stereocentres

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2α,5β,7β,10β,13α)-4-(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
(2α,5β,7β,10β,13α)-4-Acetoxy-1,7,10-trihydroxy-13-{[(2R,3S)-2-hydroxy-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate [ACD/IUPAC Name]
(2α,5β,7β,10β,13α)-4-Acetoxy-1,7,10-trihydroxy-13-{[(2R,3S)-2-hydroxy-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl-benzoat [German] [ACD/IUPAC Name]
(2α,5β,7β,10β,13α)-4-Acetoxy-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
(5β,7β,10β,13α)-4-Acetoxy-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
114977-28-5 [RN]
Benzenepropanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6, 11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)- [ACD/Index Name]
Benzenepropanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-
Benzoate de (2α,5β,7β,10β,13α)-4-acétoxy-1,7,10-trihydroxy-13-{[(2R,3S)-2-hydroxy-3-({[(2-méthyl-2-propanyl)oxy]carbonyl}amino)-3-phénylpropanoyl]oxy}-9-oxo-5,20-époxytax-11-én-2-yle [French] [ACD/IUPAC Name]
DA4172750
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6621 [DBID]
699121PHCA [DBID]
01885_FLUKA [DBID]
4290183 [DBID]
ANX-514 [DBID]
C11231 [DBID]
nchembio.2007.34-comp7 [DBID]
nchembio853-comp8 [DBID]
NSC-628503 [DBID]
RP 56976 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Ester; Drug; Antineoplastic Agent; Antineoplastic Agent, Phytogenic; Antimalarial; Radiation-Sensitizing Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D3501

    • Safety:

      L01CD02 Wikidata Q420436

    • Target Organs:

      Bcl-2 inhibitor; Microtubule Assosiated inhibitor TargetMol T1034

    • Chemical Class:

      A tetracyclic diterpenoid that is paclitaxel with the <element>N</element>-benzyloxycarbonyl group replaced by <element>N</element>-<ital>tert</ital>-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group. ChEBI CHEBI:4672
      A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position ; 10 replaced by a hydroxy group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4672
      A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group. ChEBI CHEBI:4672

    • Bio Activity:

      Bcl-2;Tubulin chain TargetMol T1034
      Binds and stabilizes microtubules; leads to cell cycle arrest and apoptosis. Displays significant antitumor activity in ovarian and gastric tumors. Prevents microtubule depolymerization and disassembl y in the absence of GTP. Exhibits cytotoxic activity. Tocris Bioscience 4056
      Binds and stabilizes microtubules; leads to cell cycle arrest and apoptosis. Displays significant antitumor activity in ovarian and gastric tumors. Prevents microtubule depolymerization and disassembly in the absence of GTP. Exhibits cytotoxic activity. Tocris Bioscience 4056
      Cell Biology Tocris Bioscience 4056
      Cell Cycle/Checkpoint TargetMol T1034
      Cell Cycle/DNA Damage MedChem Express HY-B0011
      Cell Cycle/DNA Damage; MedChem Express HY-B0011
      Cytoskeleton and Motor Proteins Tocris Bioscience 4056
      Docetaxel(Taxotere), an analog of taxol, is an inhibitor of depolymerisation of microtubules through binding to stabilized microtubules. MedChem Express
      Docetaxel(Taxotere), an analog of taxol, is an inhibitor of depolymerisation of microtubules through binding to stabilized microtubules.; IC50 Value:; Target: Microtubule/Tubulin; in vitro: IC50 concentrations (reducing survival by 50%) ranged from 0.13-3.3 ng/ml, with three neuroblastoma lines proving most sensitive and three breast and two colon carcinoma lines showing least sensitivity [1]. MedChem Express HY-B0011
      Docetaxel(Taxotere), an analog of taxol, is an inhibitor of depolymerisation of microtubules through binding to stabilized microtubules.;IC50 Value:;Target: Microtubule/Tubulin;In vitro: IC50 concentrations (reducing survival by 50%) ranged from 0.13-3.3 ng/ml, with three neuroblastoma lines proving most sensitive and three breast and two colon carcinoma lines showing least sensitivity [1]. Docetaxel was shown to promote the assembly of microtubule protein without GTP in vitro, but no inhibitory effect on DNA, RNA and protein synthesis [2]. Gene expression changes induced by paclitaxel treatment were mainly enriched in actin cytoskeleton (ACTC1, MYL2 and MYH2), tyrosine-protein kinases (ERRB4, KIT and TIE1) and focal adhesion pathway (MYL2, IGF1 and FLT1), while the expression alterations responding to docetaxel were highly co-related to cell surface receptor linked signal transduction (SHH, DRD5 and ADM2), cytokine-cytokine receptor interaction (IL1A and IL6) and cell cycleregulat MedChem Express HY-B0011
      Microtubule stabilizer Tocris Bioscience 4056
      Microtubule/Tubulin MedChem Express HY-B0011
      Microtubules Tocris Bioscience 4056

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 900.5±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 137.1±3.0 kJ/mol
Flash Point: 498.4±34.3 °C
Index of Refraction: 1.618
Molar Refractivity: 205.2±0.4 cm3
#H bond acceptors: 15
#H bond donors: 5
#Freely Rotating Bonds: 13
#Rule of 5 Violations: 4
ACD/LogP: 6.55
ACD/LogD (pH 5.5): 3.54
ACD/BCF (pH 5.5): 290.37
ACD/KOC (pH 5.5): 2016.46
ACD/LogD (pH 7.4): 3.54
ACD/BCF (pH 7.4): 290.26
ACD/KOC (pH 7.4): 2015.70
Polar Surface Area: 224 Å2
Polarizability: 81.4±0.5 10-24cm3
Surface Tension: 66.2±5.0 dyne/cm
Molar Volume: 585.7±5.0 cm3

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