Cephalomannine

Names

[ Name ]:
Cephalomannine

[Synonym ]:
Paclitaxel Related CoMpound A
(2α,5β,7β,10β,13α)-4,10-Diacetoxy-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methylbut-2-enoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
Benzenepropanoic acid, α-hydroxy-β-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecah ydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-
benzenepropanoic acid, α-hydroxy-β-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]amino]-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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 ester, (αR,βS)-
chephalomannine
(2α,5β,7β,10β,13α)-4,10-Diacetoxy-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methyl-2-butenoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
3'-N-(trans-2-methyl-2-butenoyl)-3'-N-debenzoylpaclitaxel
CEPHALOMANNINE:BENZENEPROPANOICACID,-HYDROXY--[(2-METHYL-1-OXO-2-BUTENYL)AMINO]-,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]OX...
caphalomannine
Paclitaxel Related Compound A (20 mg) (Ce-phalomannine)
(2α,5β,7β,10β,13α)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-{[(2R,3S)-2-hydroxy-3-{[(2E)-2-methylbut-2-enoyl]amino}-3-phenylpropanoyl]oxy}-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
TAXOL B
CEPHALOMANNINE:BENZENEPROPANOICACID,-HYDROXY--[(2-METHYL-1-OXO-2-BUTENYL)AMINO]-,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
CEPHALOMANNINE (TAXOL B)
CEPHALOMANNINE(P)

Biological Activity

[Description]:

Cephalomannine is a taxol derivative with antitumor, antiproliferative properties. IC50 value:Target: Cephalomannine is an active anti-cancer agent obtained from Taxus yunnanensis and has an antineoplastic effect on tumors found in mice. Cephalomannine is a chemotherapy drug that is given as a treatment for some types of cancer. Cephalomannine is most commonly used to treat non-small cell lung cancer.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

[References]

[1]. T. Grobosch, B. Schwarze, D. Stoecklein et al. Fatal poisoning with Taxus baccata. Quantification of Paclitaxel (taxol A), 10-Deacetyltaxol, Baccatin III, 10-Deacetylbaccatin III, Cephalomannine (taxol B), and 3,5-Dimethoxyphenol in Body Fluids by Liquid

[2]. Jing Zhang et al., Simultaneous Determination of 10-Deacetylbaccatin，Cephalomannine and Taxol in Different Parts of Taxus Media with Different Growth Years by UPLC. Applied Mechanics and Materials. 2011, 108, 326.

[3]. Chang Z, Guo N, Liu T, et al. Distribution and variation of paclitaxel and cephalomannine contents in wild Taxus cuspidata. Zhongguo Zhong Yao Za Zhi. 2011 Feb;36(3):294-8.

[4]. R Matesanz, J Rodríguez-Salarichs, B Pera, et al. Modulation of Microtubule Interprotofilament Interactions by Modified Taxanes. Biophysical Journal, 2011,101(12): 2970-2980.

[5]. Elena Riva, Martin Mattarella, Stella Borrelli, et al. Preparation of Fluorescent Tubulin Binders. ChemPlusChem. Early View (Online Version of Record published before inclusion in an issue)

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
929.5±65.0 °C at 760 mmHg

[ Melting Point ]:
139-141ºC

[ Molecular Formula ]:
C₄₅H₅₃NO₁₄

[ Molecular Weight ]:
831.901

[ Flash Point ]:
516.0±34.3 °C

[ Exact Mass ]:
831.346619

[ PSA ]:
221.29000

[ LogP ]:
6.59

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.615

[ Storage condition ]:
-20°C Freezer

[ Water Solubility ]:
DMSO: 14 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
37/38-41

[ Safety Phrases ]:
26-39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2932999022

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999022

Articles

Determination of paclitaxel and related taxanes in bulk drug and injectable dosage forms by reversed phase liquid chromatography.

Anal. Chem. 69(11) , 2008-16, (1997)

Baseline separation of 15 taxanes including paclitaxel (Taxol) was achieved on pentafluorophenyl (PFP) HPLC columns. Methods using aqueous acetonitrile gradients on each of two commercial PFP columns ...

Determination of cephalomannine in rat plasma by gradient elution UPLC-MS/MS method.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 963 , 70-4, (2014)

A rapid, sensitive and selective ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) was developed and validated for the determination and pharmacokinetic investigation of ce...

Microbial transformation of cephalomannine by Luteibacter sp.

J. Nat. Prod. 70(12) , 1846-9, (2007)

Luteibacter sp., a new bacterium isolated from the soil around a Taxus cuspidata Sieb. et Zucc plant, was studied for its capability to metabolize cephalomannine (1). After preparative fermentation, e...