WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H326722
CAS#: 71610-00-9
Description: Cephalomannine, also known as NSC 318735 or taxol B, is a taxol derivative with antitumor, antiproliferative properties.
Hodoodo Cat#: H326722
Name: Cephalomannine
CAS#: 71610-00-9
Chemical Formula: C45H53NO14
Exact Mass: 831.35
Molecular Weight: 831.912
Elemental Analysis: C, 64.97; H, 6.42; N, 1.68; O, 26.92
Synonym: NSC 318735; NSC 318735; NSC318735; Cephalomannine, taxol B.
IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12-(benzoyloxy)-4,11-dihydroxy-9-(((2R,3S)-2-hydroxy-3-((E)-2-methylbut-2-enamido)-3-phenylpropanoyl)oxy)-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate
InChi Key: DBXFAPJCZABTDR-WBYYIXQISA-N
InChi Code: InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
SMILES Code: [H][C@@]1([C@@H]([C@@](C2(C)C)(C[C@@H](C(C)=C2[C@H](C([C@]([C@H](C[C@]34[H])O)1C)=O)OC(C)=O)OC([C@@H]([C@H](C5=CC=CC=C5)NC(/C(C)=C/C)=O)O)=O)O)OC(C6=CC=CC=C6)=O)[C@@]3(CO4)OC(C)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 831.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Ullah A, Leong SW, Wang J, Wu Q, Ghauri MA, Sarwar A, Su Q, Zhang Y. Cephalomannine inhibits hypoxia-induced cellular function via the suppression of APEX1/HIF-1α interaction in lung cancer. Cell Death Dis. 2021 May 14;12(5):490. doi: 10.1038/s41419-021-03771-z. PMID: 33990544; PMCID: PMC8121842.
2: Helson L. Cephalomannine and 10-deacetyltaxol cytotoxicity in human glial and neuroblastoma cell-lines. Int J Oncol. 1993 Feb;2(2):297-9. PMID: 21573554.
3: Wang XS, Sun JC, Yang RN, Ren J, Liang S, Sun M, Wang YF, Gao SG. Determination of cephalomannine in rat plasma by gradient elution UPLC-MS/MS method. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 15;963:70-4. doi: 10.1016/j.jchromb.2014.05.045. Epub 2014 Jun 2. PMID: 24929960.
4: Li J, Dai J, Chen X, Zhu P. Microbial transformation of cephalomannine by Luteibacter sp. J Nat Prod. 2007 Dec;70(12):1846-9. doi: 10.1021/np0701531. Epub 2007 Nov 15. Erratum in: J Nat Prod. 2008 Apr;71(4):742. PMID: 18001087.
5: Glowniak K, Zgórka G, Józefczyk A, Furmanowa M. Sample preparation for taxol and cephalomannine determination in various organs of Taxus sp. J Pharm Biomed Anal. 1996 Jun;14(8-10):1215-20. doi: 10.1016/s0731-7085(96)01728-1. PMID: 8818036.
6: Zhang JW, Ge GB, Liu Y, Wang LM, Liu XB, Zhang YY, Li W, He YQ, Wang ZT, Sun J, Xiao HB, Yang L. Taxane's substituents at C3' affect its regioselective metabolism: different in vitro metabolism of cephalomannine and paclitaxel. Drug Metab Dispos. 2008 Feb;36(2):418-26. doi: 10.1124/dmd.107.018242. Epub 2007 Nov 26. PMID: 18039807.
7: Chmurny GN, Hilton BD, Brobst S, Look SA, Witherup KM, Beutler JA. 1H- and 13C-nmr assignments for taxol, 7-epi-taxol, and cephalomannine. J Nat Prod. 1992 Apr;55(4):414-23. doi: 10.1021/np50082a002. PMID: 1355110.
8: Chang Z, Guo N, Liu T, Zhou Z, Wang Y. [Distribution and variation of paclitaxel and cephalomannine contents in wild Taxus cuspidata]. Zhongguo Zhong Yao Za Zhi. 2011 Feb;36(3):294-8. Chinese. PMID: 21585029.
9: Gao F, Wang D, Huang X. Synthesis, isolation, stereostructure and cytotoxicity of paclitaxel analogs from cephalomannine. Fitoterapia. 2013 Oct;90:79-84. doi: 10.1016/j.fitote.2013.07.011. Epub 2013 Jul 20. PMID: 23876369.
10: Zhang RY, Liu ZK, Wei D, Yong YL, Lin P, Li H, Liu M, Zheng NS, Liu K, Hu CX, Yang XZ, Chen ZN, Bian H. UBE2S interacting with TRIM28 in the nucleus accelerates cell cycle by ubiquitination of p27 to promote hepatocellular carcinoma development. Signal Transduct Target Ther. 2021 Feb 16;6(1):64. doi: 10.1038/s41392-020-00432-z. PMID: 33589597; PMCID: PMC7884418.
11: Peng S, Chen X, Huang C, Yang C, Situ M, Zhou Q, Ling Y, Huang H, Huang M, Zhang Y, Cheng L, Zhang Q, Guo Z, Lai Y, Huang J. UBE2S as a novel ubiquitinated regulator of p16 and β-catenin to promote bone metastasis of prostate cancer. Int J Biol Sci. 2022 May 16;18(8):3528-3543. doi: 10.7150/ijbs.72629. PMID: 35637955; PMCID: PMC9134922.
12: Moyna G, Mediwala S, Williams HJ, Scott AI. A simple algorithm for superimposing sets of NMR derived structures: its application to the conformational study of cephalomannine in lipophobic and lipophilic solution. J Chem Inf Comput Sci. 1996 Nov-Dec;36(6):1224-7. doi: 10.1021/ci960118s. PMID: 8941997.
13: Li Y, Qin F, Wang SM, Guo RX, Zhang YF, Gu YC, Shi QW. Chemical studies on Taxus canadensis. Chem Biodivers. 2013 Oct;10(10):1729-53. doi: 10.1002/cbdv.201200032. PMID: 24130020.
14: Grobosch T, Schwarze B, Stoecklein D, Binscheck T. 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 chromatography-tandem mass spectrometry. J Anal Toxicol. 2012 Jan-Feb;36(1):36-43. doi: 10.1093/jat/bkr012. PMID: 22290751.
15: Xue B, Zhao J, Fan Y, Chen S, Li W, Chen J, Li Z, Wang H, Kong H. Synthesis of Taxol and Docetaxel by Using 10-Deacetyl-7-xylosyltaxanes. Chem Biodivers. 2020 Feb;17(2):e1900631. doi: 10.1002/cbdv.201900631. Epub 2020 Jan 22. PMID: 31967396.
16: Zhang YY, Liu Y, Zhang JW, Ge GB, Liu HX, Wang LM, Sun J, Yang L. C-7 configuration as one of determinants in taxanes metabolism by human cytochrome P450 enzymes. Xenobiotica. 2009 Dec;39(12):903-14. doi: 10.3109/00498250903271989. PMID: 19795923.
17: Vivekanandan K, Swamy MG, Prasad S, Mukherjee R, Burman AC. Identification of isocephalomannine in the presence of cephalomannine isomers and alkali metal ion adducts in a paclitaxel active pharmaceutical ingredient using electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(11):1731-5. doi: 10.1002/rcm.2500. PMID: 16676315.
18: Dell'Anno I, Melani A, Martin SA, Barbarino M, Silvestri R, Cipollini M, Giordano A, Mutti L, Nicolini A, Luzzi L, Aiello R, Gemignani F, Landi S. A Drug Screening Revealed Novel Potential Agents against Malignant Pleural Mesothelioma. Cancers (Basel). 2022 May 20;14(10):2527. doi: 10.3390/cancers14102527. PMID: 35626133; PMCID: PMC9139775.
19: Kingston DG, Gunatilaka AA, Ivey CA. Modified taxols, 7. A method for the separation of taxol and cephalomannine. J Nat Prod. 1992 Feb;55(2):259-61. doi: 10.1021/np50080a022. PMID: 1352536.
20: Beckvermit JT, Anziano DJ, Murray CK. An Improved Method for Separating Paclitaxel and Cephalomannine Using Ozone and Girard Reagents. J Org Chem. 1996 Dec 13;61(25):9038-9040. doi: 10.1021/jo961402l. PMID: 11667894.
