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C4991

Sigma-Aldrich

Cephalomannine

≥97% (HPLC), solid

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Synonym(s):
NSC 318735
Empirical Formula (Hill Notation):
C45H53NO14
CAS Number:
Molecular Weight:
831.90
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥97% (HPLC)

form

solid

solubility

DMSO: soluble 14 mg/mL

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

storage temp.

room temp

SMILES string

C\C=C(/C)C(=O)N[C@H]([C@@H](O)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)C4[C@@](C)([C@@H](O)C[C@H]5OC[C@@]45OC(C)=O)C(=O)[C@H](OC(C)=O)C(=C1C)C2(C)C)c6ccccc6

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

InChI key

DBXFAPJCZABTDR-UJLUYDJNSA-N

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1 of 4

This Item
PHR2111C8395C6895
vibrant-m

C4991

Cephalomannine

vibrant-m

PHR2111

Paclitaxel Related Compound A

vibrant-m

C8395

Cephradine

vibrant-m

C6895

Cefaclor

form

solid

form

-

form

powder

form

powder or crystals

Quality Level

100

Quality Level

300

Quality Level

200

Quality Level

200

solubility

DMSO: soluble 14 mg/mL

solubility

-

solubility

ethanol: practically insoluble 96%, hexane: practically insoluble, water: slightly soluble

solubility

soluble (slightly soluble in water, practically insoluble in methanol, ethanol)

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

General description

Chemical structure: ß-lactam

Application

Cephalomannine has been used for the identification of fungal taxol (anti-cancer drug) in liquid culture.

Biochem/physiol Actions

Cephalomannine is isolated from Taxus wallichiana, and serves as an antifungal agent.
Cephalomannine is a taxol derivative with antitumor, antiproliferative properties.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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D D Woo et al.
Kidney international, 51(5), 1613-1618 (1997-05-01)
Homozygous cpk/cpk mice develop polycystic kidney disease and die of uremia between the fourth and fifth weeks of age. Cpk/cpk mice treated weekly with paclitaxel (Taxol) can live to over six months of age. This dramatic moderation of polycystic kidney
D Song et al.
Journal of chromatography. B, Biomedical applications, 663(2), 337-344 (1995-01-20)
This report describes the analysis of taxol in human plasma, cell culture medium, and dog bladder tissue by isocratic high-performance liquid chromatography (HPLC) with automated column switching. Cephalomannine was used as the internal standard. Biological samples were extracted with ethyl
K Glowniak et al.
Journal of pharmaceutical and biomedical analysis, 14(8-10), 1215-1220 (1996-06-01)
Solid-phase extraction and preparative thin-layer chromatography were applied as sample preparation techniques for the purification of crude extracts from twigs and needles of various Taxus species as well as for the isolation of taxol and cephalomannine for further reversed phase
Corwin Hansch et al.
Molecular pharmaceutics, 6(3), 849-860 (2009-04-02)
The microtubule-stabilizing taxanes such as paclitaxel and docetaxel are the two most important anticancer drugs currently used in clinics for the treatment of various types of cancers. However, the major common drawbacks of these two drugs are drug resistance, neurotoxicity
Synthesis and Chemistry of Agrochemicals V, 686 (1998)

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