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33069-62-4 molecular structure
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(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

ChemBase ID: 72546
Molecular Formular: C47H51NO14
Molecular Mass: 853.90614
Monoisotopic Mass: 853.33095532
SMILES and InChIs

SMILES:
c1cccc(c1)C(=O)N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(C(C(=C1C)[C@H](C(=O)[C@]1(C([C@]3([C@@H](C[C@@H]1O)OC3)OC(=O)C)[C@@H]2OC(=O)c1ccccc1)C)OC(=O)C)(C)C)O)O)c1ccccc1
Canonical SMILES:
CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@@H]3[C@](C2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
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-VAZQATRQSA-N

Cite this record

CBID:72546 http://www.chembase.cn/molecule-72546.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
IUPAC Traditional name
@paclitaxel
Synonyms
Onxol
Taxol
Nov-Onxol
Paclitaxel(Taxol)
CAS Number
33069-62-4
PubChem SID
162037471
PubChem CID
441276

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1150 external link Add to cart Please log in.
Data Source Data ID
PubChem 441276 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors 10  H Donor
LogD (pH = 5.5) 3.5388339  LogD (pH = 7.4) 3.538369 
Log P 3.53884  Molar Refractivity 218.2945 cm3
Polarizability 86.54275 Å3 Polar Surface Area 221.29 Å2
Rotatable Bonds 14  Lipinski's Rule of Five false 
Acid pKa 10.364198 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Storage Condition
-20°C expand Show data source
Target
Microtubule Formation expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1150 external link
Research Area
Description Cancer
Biological Activity
Description Paclitaxel (Taxol, Onxol, Nov-Onxol) is a microtubule polymer stabilizer with IC50 of 0.1 pM in human endothelial cells.
Targets Microtubule (human endothelial cells)
IC50 0.1 pM [1]
In Vitro Paclitaxel inhibits non-endothelial type human cells at 104 - to 105 -fold higher concentrations, with IC50 of 1 nM-10 nM. The selectivity of Paclitaxel inhibition of cell proliferation is also species specific, as mouse ECs are not sensitive to Paclitaxel at ultra low concentrations. Inhibition of human ECs by Paclitaxel at ultra low concentrations does not affect the cellular microtubule structure, and the treated cells do not show G2/M cell cycle arrest and apoptosis, suggesting a novel but as yet unidentified mechanism of action. In an in vitro angiogenesis assay, Paclitaxel at ultra low concentrations blocks human ECs from forming sprouts and tubes in the three-dimensional fibrin matrix. [1] In the presence of SMF, the efficient concentration of Paclitaxel on K562 cells is decreased from 50 to 10 ng/mL. The cell cycle arrest effect of Paclitaxel with or without SMF on K562 cells is correlated with DNA damage. [2] Paclitaxel alone causes a time-dependent inhibition of CDK1 in four cell lines including A549 cells, H358, H1395 cells and H1666 cells. [3]
In Vivo The inhibition rations of Paclitaxel alone on BC-V and BC-ER tumors are 49.78% and 51.23%, respectively. Treatment of six cycles of 20 mg/kg Paclitaxel significantly reduces the percentages of Ki-67-positive cells to 20.4% in BC-V tumors and 25.1% in BC-ER tumors, respectively. [5]
Clinical Trials Paclitaxel has entered in a Phase III clinical trial for the treatment of tubular breast cancer stage II, mucinous breast cancer stage II, breast cancer female NOS and invasive ductal breast cancer.
Features
Combination Therapy
Description K562 cells treated with SMF plus Paclitaxel are arrested at the G2 phase, which is mainly induced by Paclitaxel. The potency of the combination of SMF and Paclitaxel is greater than that of SMF or Paclitaxel alone on K562 cells, and these effects are correlated with DNA damage induced by SMF and Paclitaxel. [2] The combination of Lobaplatin with antitubulin agents, especially with Paclitaxel, leads to significantly enhanced activity, which is superior to that of Cisplatin combined with antitubulin agents. [4] Paclitaxel in combination with Carboplatin, BIBW 2992, and Bevacizumab or BIBW2992 is currently under investigation in a Phase I clinical trial for the treatment of neoplasms.
Protocol
Cell Assay [1]
Cell Lines Cells including human neonatal dermal microvascular ECs (HMVECs), human umbilical vein ECs (HUVECs), human umbilical artery ECs (HUAVECs), normal human astrocytes (NHAs), normal human dermal fibroblasts (NHDFs), normal human epidermal keratinocytes (NHEKs), human mammary epithelial cells (HMEpCs), human prostate epithelial cells (PrEpCs) and human umbilical artery smooth muscle cells (UASMCs)
Concentrations 0.1-100 pM
Incubation Time 72 hours
Methods Cells including human neonatal dermal microvascular ECs (HMVECs), human umbilical vein ECs (HUVECs), human umbilical artery ECs (HUAVECs), normal human astrocytes (NHAs), normal human dermal fibroblasts (NHDFs), normal human epidermal keratinocytes (NHEKs), human mammary epithelial cells (HMEpCs), human prostate epithelial cells (PrEpCs) and human umbilical artery smooth muscle cells (UASMCs) are cultured. Cell proliferations are performed in 96-well plates using cells between passages 6 and 12. Cells are seeded at 3000–5000 cells/well and allowed to attach for 4 hours. Paclitaxel, diluted in culture medium, is added in quadruplicate wells and the cells ae incubated for 3 days before MTS reagents are added to quantitate the live cells in each well.
Animal Study [5]
Animal Models Female, 20-22 g homozygous nude athymic mice with BC-V and BC-ER tumors
Formulation Control
Doses 20 mg/kg
Administration Administered via i.v.
References
[1] Wang J, et al. Anticancer Drugs. 2003, 14(1), 13-19.
[2] Sun RG, et al. Gen Physiol Biophys. 2012, 31(1), 1-10.
[3] Zhang XH, et al. Cancer Lett. 2012, 322(2), 213-222.
[4] Xie CY, et al. Anticancer Drugs. 2012.
[5] Chang J, et al. Breast Cancer Res Treat. 2012.

PATENTS

PATENTS

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INTERNET

INTERNET

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