Molecule

ID:1098

General Information
Structure
MolImage
Molecular Formula
C₄₇H₅₁NO₁₄
Molecular Mass
853.90614
Exact Mass
853.33095532
Charge
0
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
Canonic 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
Isomeric Smiles
[C@H]1(OC(=O)c2ccccc2)[C@@H]2[C@@]3(CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@@H](C2=C([C@H](C[C@]1(O)C2(C)C)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C)OC(=O)C)C)O)OC(=O)C
Calculated Properties
JChem
LogD (pH = 7.4)
3.54
LogD (pH = 5.5)
3.54
Log P
3.54
Rotatable Bonds
14
H Donor
4
H Acceptors
10
Lipinski's Rule of Five
false
Acid pKa
11.93
Polar Surface Area
221.29
Polarizability
87.13
Molar Refractivity
218.29
LOG S
-6.77
Names and Identifiers
Brand Name
LipoPacOnxolAbraxaneTaxolVascular WrapEpitaxolPaxceedTaxol AXoranePaxene
Synonyms
7-EpitaxolABI-0077-epi-Taxol7-epi-PaclitaxelPaclitaxel7-EpipaclitaxelTaxol®YewtaxanOncoGelNSC 125973(-)-PaclitaxelGenetaxylTaxolPacliexOnxalAbraxaneGenaxolPaclitaxelTaxol AAnzataxTAXOLtaxol5beta,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-phenylisoserinePaclitaxel(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 esterTaxol Apaclitaxel
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[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate (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 (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
TAX taxol paclitaxel (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 (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[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
API Name
Paclitaxel
Registration numbers
PubChem CID
36314
IUPHAR ligand ID
2770
Chemspider ID
10368587
Unique Ingredient Identifier
P88XT4IS4D
DrugBank ID
DB01229
CAS Number
33069-62-4
Wikipedia Title
Paclitaxel
MDL Number
MFCD00869953
Patent number
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KNApSAcK Database
C00002365
PDBeChem Database
TA1
CompTox Database
DTXSID9023413
SureChEMBL Database
SCHEMBL3976
VirtualMetabolicHuman Database
taxol
Reactom Database
R-HSA-211910
BindingDB Database
50001839
ACToR Database
33069-62-4
ArrayExpress (Repository of Microarray data)
E-TOXM-9
KEGG DRUG Database
D00491
SABIO-RK Database
14410
Rhea Database
RHEA:33687
ArrayExpress (Gene Expression Altlas)
E-GEOD-28784E-GEOD-12791
Drug Central Database
2,044
Properties
Physical Property
Solubility
Insoluble
Methanol
Hydrophobicity(logP)
3
Melting Point
213-223°C
214-216°C
Vapor Pressure
< 1.12 x 10-7 Torr
Apperance
White Solid
Powder
Pharmacology Properties
Excretion
Fecal and urinary
Metabolism
Hepatic (CYP2C8 and CYP3A4)
Admin Routes
iv
Half Life
5.8 hours
Pregnancy Category
D (US)
Bioavailability
6.5% (oral)
Legal Status
Rx-only (US)
Protein Bound
89 to 98%
Mechanism of Action
Binds to the beta subunit of tubulin
Interferes with the normal function of microtubule growth by hyper-stabilisation of their structure
Safety Information
Australian Hazchem
2X
Emergency Response Guidebook(ERG) Number
154
RTECS
DA8340700
Hazard Class
6.1
European Hazard Symbols
Toxic Toxic (T)
Safety Statements 
S:28-36/37/39-45-53
Packing Group
III
MSDS Link
EU Hazard Identification Number
6.1B
EU Classification
T2
Risk Statements 
R:25
UN Number
2811
Storage Condition
Room Temperature (15-30°C)
-20°C Freezer
Product Information
Purity
>98%
95+%
Certificate of Analysis
Application(s)
Biochemical tool extensively used to study cellular shape and function.
Use limited by low solubility and scarce availability of Taxus brevifolia bark
Antileukaemic and antineoplastic agent, esp. against melanoma and ovarian tumours
Also shown to be active against oomycete fungi
Biological Source
Isol. from the stem bark of Taxus brevifolia and Taxus cuspidata (Taxaceae)
Molecular Spectra
No Data Available
Click here to submit data
Molecule Details
References
PubChem Literature
From Data Sources
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