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Inherent Properties, Identifiers and References
ChemSpider ID: 10368587
Empirical Formula: C47H51NO14
Molecular Weight: 853.9061
Nominal Mass: 853 Da
Average Mass: 853.9061 Da
Monoisotopic Mass: 853.330955 Da
Systematic Name:
SMILES: O=C(N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@H]5C[C@@]6(O)[C@@H](OC(=O)​c2ccccc2)[C@H]3[C@@](C)([C@@H](O)C[C@H]4OC[C@@]34OC(C)=O)C(=O)[C@​H](OC(C)=O)\C(=C5/C)[C@]6(C)C)c7ccccc7
InChI: InChI=1/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(59-2​6(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6​H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChIKey: RCINICONZNJXQF-MZXODVADBJ
(Details...) Wikipedia Article(s)
Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It was discovered in a National Cancer Institute program at the Research Triangle Institute in 1967 when Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia and named it 'taxol'. When it was developed commercially by Bristol-Myers Squibb (BMS) the generic name was changed to 'paclitaxel' and the BMS compound is sold under the trademark 'Taxol'. In this formulation paclitaxel is dissolved in Cremophor EL, as a delivery agent. A newer formulation, in which paclitaxel is bound to albumin, is sold under the trademark Abraxane. Paclitaxel is now used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanced forms of Kaposi's sarcoma. Paclitaxel is also used for the prevention of restenosis. Paclitaxel works by interfering with normal microtubule breakdown during cell division. Together with docetaxel, it forms the drug category of the taxanes. It was the subject of a notable total synthesis by Robert A. Holton. As well as offering substantial improvement in patient care, paclitaxel has been a relatively controversial drug. There was originally concern because of the environmental impact of its original sourcing, no longer used, from the Pacific yew. In addition, the assignment of rights, and even the name itself, to Bristol-Myers Squibb were the subject of public debate and Congressional hearings. Read more... or Edit at Wikipedia...
(Details...) Original Reference(s) Filter
Data Source External ID(s)
ChemZoo N/A
DailyMed N/A, N/A, N/A, N/A, N/A, N/A, N/A, N/A
EPA DSSTox 873_FDAMDD_v3b
FDA 20262
Journal of Heterocyclic Chemistry 19970675_1
Nature Chemical Biology nchembio.2007.34-comp9
Oxford University Chemical Safety Data N/A, N/A
Sigma-Aldrich Substance Vendors T1912_SIGMA, T7191_SIGMA, T7402_SIGMA
Single Depositions paclitaxel, taxol
Wikipedia Paclitaxel
Disclaimer (Details...) Supplemental Information

User Data

  • experimental physchem properties
    • Melting Point: 213 - 216 C
  • miscellaneous
    • Appearance: white crystalline powder
    • Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
    • Toxicity: IPR-RAT LD50 33 mg kg-1, IPR-MUS LD50 128 mg kg-1
    • Safety: Safety glasses, gloves. Do not breathe dust.
(Details...) Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(1S,2S,3R​,4S,7R,9S​,10S,12R,​15S)-4,12​-bis(acet​yloxy)-1,​9-dihydro​xy-15-({(​2R,3S)-2-​hydroxy-3​-phenyl-3​-[(phenyl​carbonyl)​amino]pro​panoyl}ox​y)-10,14,​17,17-tet​ramethyl-​11-oxo-6-​oxatetrac​yclo[11.3​.1.0~3,10​~.0~4,7~]​heptadec-​13-en-2-y​l benzoate

(1S,2S,3R​,4S,7R,9S​,10S,12R,​15S)-4,12​-Bis(acet​yloxy)-1,​9-dihydro​xy-15-({(​2R,3S)-2-​hydroxy-3​-phenyl-3​-[(phenyl​carbonyl)​amino]pro​panoyl}ox​y)-10,14,​17,17-tet​ramethyl-​11-oxo-6-​oxatetrac​yclo[11.3​.1.0~3,10​~.0~4,7~]​heptadec-​13-en-2-y​lbenzolca​rboxylat

(2alpha,5​beta,7bet​a,10beta,​13alpha)-​4,10-bis(​acetyloxy​)-1,7-dih​ydroxy-13​-({(2R,3S​)-2-hydro​xy-3-phen​yl-3-[(ph​enylcarbo​nyl)amino​]propanoy​l}oxy)-9-​oxo-5,20-​epoxytax-​11-en-2-y​l benzoate

,13-tetra​methyl-5-​oxo-7,11-​methano-1​H-cyclode​ca[3,4]be​nz[1,2-b]​oxet-9-yl​ ester, (​alphaR,be​taS)-

33069-62-4 [RN]

5b,20-Epo​xy-1,2a,4​,7b,10b,1​3a-hexahy​droxytax-​11-en-9-o​ne 4,10-D​iacetate ​2-Benzoat​e 13-Este​r with (2​R,3S)-N-B​enzoyl-3-​phenyliso​serine

Anzatax

benzenepr​opanoic a​cid, beta​-(benzoyl​amino)-al​pha-hydro​xy-, (2aR​,4S,4aS,6​R,9S,11S,​12S,12aR,​12bS)-6,1​2b-bis(ac​etyloxy)-​12-(benzo​yloxy)-2a​,3,4,4a,5​,6,9,10,1​1,12,12a,​12b-dodec​ahydro-4,​11-dihydr​oxy-4a,8,​13

benzenepr​opanoic a​cid, beta​-(benzoyl​amino)-al​pha-hydro​xy-, (2aR​,4S,4aS,6​R,9S,11S,​12S,12aR,​12bS)-6,1​2b-bis(ac​etyloxy)-​12-(benzo​yloxy)-2a​,3,4,4a,5​,6,9,10,1​1,12,12a,​12b-dodec​ahydro-4,​11-dihydr​oxy-4a,8,​13,13-tet​ramethyl-​5-oxo-7,1​1-methano​-1H-cyclo​deca[3,4]​benz[1,2-​b]oxet-9-​yl ester,​ (alphaR,​betaS)-

benzoate ​de (1S,2S​,3R,4S,7R​,9S,10S,1​2R,15S)-4​,12-bis(a​cétyloxy)​-1,9-dihy​droxy-15-​({(2R,3S)​-2-hydrox​y-3-phény​l-3-[(phé​nylcarbon​yl)amino]​propanoyl​}oxy)-10,​14,17,17-​tétraméth​yl-11-oxo​-6-oxatét​racyclo[1​1.3.1.0~3​,10~.0~4,​7~]heptad​éc-13-én-​2-yle

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(Details...) Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ABI 007

DRG 0190

HSDB 6839

QW 8184

nchembio.​2007.34-c​omp9

NSC 125973

T1912_SIG​MA

T7191_SIG​MA

T7402_SIG​MA

(Details...) Predicted Properties
LogP: ACD/LogP: 7.38
# of Rule of 5 Violations: 3
ACD/LogD (pH 5.5): 7.38 ACD/LogD (pH 7.4): 7.38
ACD/BCF (pH 5.5): 237938.83 ACD/BCF (pH 7.4): 237929.42
ACD/KOC (pH 5.5): 245498.58 ACD/KOC (pH 7.4): 245488.88
#H bond acceptors: 15 #H bond donors: 4
#Freely Rotating Bonds: 17 Polar Surface Area: 221.29 Å2
Index of Refraction: 1.637 Molar Refractivity: 219.26 cm3
Molar Volume: 610.5 cm3 Polarizability: 86.92 10-24cm3
Surface Tension: 68.4 dyne/cm Density: 1.39 g/cm3
Flash Point: 532.6 °C Enthalpy of Vaporization: 145.98 kJ/mol
Boiling Point: 957.1 °C at 760 mmHg Vapour Pressure: 0 mmHg at 25°C
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 0, 1, 0, 0, 0, 14, 4, 0, 3, 6, 23, 15, 8, 0, 18, 10, 6, 1, 3, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor1fm90.03
KinasesSRC, tyrosine kinase SRC2src0.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
Other EnzymesHIVPR, HIV protease1hpx0.01
MetalloenzymesPDE5, phosphodiesterase 51xp00.01
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.00
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.00
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.00
Nuclear Hormone ReceptorsPR, progesterone receptor1sr70.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
MetalloenzymesACE, angiotensin-converting enzyme1o860.00
KinasesVEGFr2, vascular endothelial growth factor receptor1vr20.00
Other EnzymesGPB, glycogen phosphorylase1a8i0.00
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase1a7a0.00
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
Serine ProteasesThrombin1ba80.00
Other EnzymesNA, neuraminidase1a4g0.00
KinasesP38 MAP, P38 mitogen activated protein1kv20.00
MetalloenzymesADA, adenosine deaminase1stw0.00
Other EnzymesAChE, acetylcholinesterase1eve0.00
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.00
KinasesHSP90, human heat shock protein 901uy60.00
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.00
Serine ProteasesFXa, factor Xa1f0r0.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
Other EnzymesCOX-2, cyclooxygenase-21cx20.00
KinasesEGFr, epidermal growth factor receptor1m170.00
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R1mvc0.00
KinasesTK, thymidine kinase1kim0.00
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