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Cephalomannine

Alias: NSC318735 NSC 318735 NSC 318735
Cat No.:V17921 Purity: ≥98%
Cephalomannine is a taxol alkaloid analog that can be extracted from most Cephalotaxus plants.
Cephalomannine
Cephalomannine Chemical Structure CAS No.: 71610-00-9
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
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Product Description
Cephalomannine is a taxol alkaloid analog that can be extracted from most Cephalotaxus plants. Cephalomannine is an orally bioactive anti-tumor agent that can be used as a chemotherapeutic agent in cancer-related research.
Cephalomannine (CAS#: 71610-00-9) is a natural taxane diterpenoid closely related to paclitaxel, isolated from the bark and leaves of the yew tree (Taxus species). It is a taxol derivative with antitumor and antiproliferative properties. Cephalomannine is active in promoting microtubule assembly and shows cytotoxicity in human glial and neuroblastoma cell lines. Cephalomannine has been shown to have antitumor effects in mice. It is used in preclinical research to study taxane-based chemotherapy, structure-activity relationships, and mechanisms of drug resistance.
Biological Activity I Assay Protocols (From Reference)
Targets
Microtubules. Cephalomannine, like other taxanes, binds to tubulin and promotes microtubule assembly. This stabilizes microtubules and prevents their depolymerization, leading to cell cycle arrest and apoptosis. Cephalomannine is active in promoting microtubule assembly and shows cytotoxicity in human glial and neuroblastoma cell lines.
ln Vitro
Cephalomannine shows cytotoxicity in human glial and neuroblastoma cell lines. It is active in promoting microtubule assembly. It has antitumor and antiproliferative properties. As a taxane derivative, its mechanism of action is similar to paclitaxel. Cephalomannine shows cytotoxicity in human glial and neuroblastoma cell lines.
ln Vivo
Cephalomannine has been shown to have antitumor effects in mice. It is used in preclinical research to study taxane-based chemotherapy, structure-activity relationships, and mechanisms of drug resistance. Specific in vivo study details are not provided. Cephalomannine has been shown to have antitumor effects in mice.
Enzyme Assay
Specific protocols for in vitro enzyme/receptor binding assays for Cephalomannine are not detailed. Its activity is typically assessed in cell-based assays measuring cytotoxicity and microtubule polymerization. Binding to tubulin can be studied using in vitro polymerization assays. Cephalomannine is active in promoting microtubule assembly.
Cell Assay
Cellular assays for Cephalomannine involve treating cancer cell lines with the compound and assessing cell viability and proliferation. Its ability to promote microtubule assembly can also be studied in cell-free systems or in cells using immunofluorescence. Cephalomannine shows cytotoxicity in human glial and neuroblastoma cell lines.
Animal Protocol
In vivo efficacy of Cephalomannine has been studied in mouse models of cancer, where it showed antitumor effects. It is used in preclinical research to study taxane-based chemotherapy. Cephalomannine has been shown to have antitumor effects in mice.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Cephalomannine is not available in the provided references. As a taxane derivative, its PK properties are likely similar to other taxanes, with poor oral bioavailability and extensive metabolism.
Toxicity/Toxicokinetics
Specific toxicological data for Cephalomannine is not available. As a taxane derivative, it is expected to have a similar toxicity profile to paclitaxel, which can include myelosuppression, neuropathy, and hypersensitivity reactions.
References

[1]. Synthesis, isolation, stereostructure and cytotoxicity of paclitaxel analogs from cephalomannine.Fitoterapia. 2013 Oct;90:79-84.

[2]. Microbial transformation of cephalomannine by Luteibacter sp. J Nat Prod. 2007 Dec;70(12):1846-9.

[3]. Cephalomannine inhibits hypoxia-induced cellular function via the suppression of APEX1/HIF-1α interaction in lung cancer. Cell death & disease vol. 2021;12(5):490.

[4]. 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.

Additional Infomation
Taxol B has been reported to exist in Taxus sumatrana, Taxus cuspidata, and other organisms with relevant data. Cefganlonine is a diterpenoid taxane extracted from the bark and leaves of Taxus brevifolia and can be converted into Taxol. (National Cancer Institute, USA)
Cephalomannine is a research compound not approved for clinical use. It is a natural product and a taxane derivative used to study the mechanisms of taxane-based chemotherapy and drug resistance. It is structurally related to paclitaxel. Cephalomannine is a natural taxane diterpenoid closely related to paclitaxel, isolated from the bark and leaves of the yew tree (Taxus species).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C45H53NO14
Molecular Weight
831.912
Exact Mass
831.346
CAS #
71610-00-9
PubChem CID
6436208
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
929.5±65.0 °C at 760 mmHg
Melting Point
139-141ºC
Flash Point
516.0±34.3 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.615
LogP
6.59
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
14
Rotatable Bond Count
14
Heavy Atom Count
60
Complexity
1790
Defined Atom Stereocenter Count
11
SMILES
C/C=C(\C)/C(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H]([C@H]4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
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
Chemical Name
[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
Synonyms
NSC318735 NSC 318735 NSC 318735
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~120.21 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.01 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (3.01 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2021 mL 6.0103 mL 12.0205 mL
5 mM 0.2404 mL 1.2021 mL 2.4041 mL
10 mM 0.1202 mL 0.6010 mL 1.2021 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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