Home > Compound List > Compound details
33069-62-4 molecular structure
click picture or here to close

(1S,2S,3R,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[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

ChemBase ID: 137569
Molecular Formular: C47H51NO14
Molecular Mass: 853.90614
Monoisotopic Mass: 853.33095532
SMILES and InChIs

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](c1ccccc1)NC(=O)c1ccccc1)O)O)OC(=O)c1ccccc1)(CO4)OC(=O)C)O)C)OC(=O)C
Canonical SMILES:
CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@@H]3[C@]([C@H]2[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-MZXODVADSA-N

Cite this record

CBID:137569 http://www.chembase.cn/molecule-137569.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2S,3R,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[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate
IUPAC Traditional name
taxol
Synonyms
Paclitaxel
CAS Number
33069-62-4
MDL Number
MFCD00869953
Beilstein Number
1420457
PubChem SID
24277878
24899998
162231831
24900422
PubChem CID
36314

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 36314 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 10.363949  H Acceptors 10 
H Donor LogD (pH = 5.5) 3.5388339 
LogD (pH = 7.4) 3.5383687  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 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: soluble50 mg/mL expand Show data source
DMSO: soluble50 mg/mL (can be stored frozen for several months) expand Show data source
ethanol: soluble expand Show data source
H2O: soluble (hydrolyzes) expand Show data source
methanol: soluble (undergoes transesterification) expand Show data source
methanol: soluble50 mg/mL, clear, colorless expand Show data source
Apperance
white powder expand Show data source
Melting Point
213 °C (dec.)(lit.) expand Show data source
Optical Rotation
[α]20/D -49°, c = 1 in methanol expand Show data source
RTECS
DA8340700 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22-37/38-41-42/43-62-68-68/20/21/22 expand Show data source
37/38-41-42/43-62-68 expand Show data source
Safety Statements
22-26-36/37/39-45 expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H315-H317-H318-H334-H335-H341-H361 expand Show data source
H315-H317-H318-H334-H335-H341-H361-H371 expand Show data source
GHS Precautionary statements
P260-P280-P305 + P351 + P338-P342 + P311 expand Show data source
P261-P280-P305 + P351 + P338-P342 + P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Gene Information
human ... BCL2(596) expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥97% expand Show data source
95% expand Show data source
Impurities
≤1% methyl alcohol and ethyl alcohol expand Show data source
≤4% water expand Show data source
natural taxane impurities, none detected(except ≤0.5% paclitaxel degradation products.) expand Show data source
Biological Source
from semisynthetic (from Taxus sp.) expand Show data source
from Taxus brevifolia expand Show data source
from Taxus yannanensis expand Show data source
Empirical Formula (Hill Notation)
C47H51NO14 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - T7191 external link
Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).
Sigma Aldrich - T1912 external link
Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).
Sigma Aldrich - T7402 external link
Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Packaging
1, 5, 25 mg in glass bottle
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).
Sigma Aldrich - 417017 external link
Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Packaging
1 mg in glass bottle
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).
Sigma Aldrich - 86346 external link
Caution
Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.
Biochem/physiol Actions
Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
    No data available
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle