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Merck

C4991

Cephalomannine

≥97% (HPLC), solid

Synonym(s):

NSC 318735

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About This Item

Empirical Formula (Hill Notation):
C45H53NO14
CAS Number:
71610-00-9
Molecular Weight:
831.90
NACRES:
NA.77
PubChem Substance ID:
24724441
UNSPSC Code:
12352200
MDL number:
MFCD01075131

Key Documents

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Product Name

Cephalomannine, ≥97% (HPLC), solid

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 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 key

DBXFAPJCZABTDR-UJLUYDJNSA-N

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

Quality Level

100

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Application

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

Biochem/physiol Actions

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

General description

Chemical structure: ß-lactam

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000403335
0000403335
0000133141
0000057412
0000019495

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Hongbo Wang et al.
Cancer letters, 268(1), 89-97 (2008-05-17)
Lx2-32c, a novel taxane derivative, is a semisynthetic analogue from cephalomannine. Its antitumor activity in vivo and in vitro was investigated in this study. Lx2-32c was cytotoxic (IC50=1.7+/-1.6nM) to various human tumor cell lines after 72h incubation. In vitro it
K C Chan et al.
Journal of chromatography. B, Biomedical applications, 657(2), 301-306 (1994-07-15)
High-performance liquid chromatography (HPLC) and micellar electrokinetic chromatography (MEKC) were applied for the separation of taxol, cephalomannine, and baccatin III in crude extracts from the needle and bark of Taxus species. The chromatogram of the bark extract was cleaner than
G Moyna et al.
Journal of chemical information and computer sciences, 36(6), 1224-1227 (1996-11-01)
A simple iterative method for superimposing sets of NMR derived structures and calculation of the root mean square deviation (RMSD) of the sets is described. It was compared to the commonly used algorithm involving pairwise best fitting in the conformational
Jiang-Wei Zhang et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(2), 418-426 (2007-11-28)
To investigate how taxane's substituents at C3' affect its metabolism, we compared the metabolism of cephalomannine and paclitaxel, a pair of analogs that differ slightly at the C3' position. After cephalomannine was incubated with human liver microsomes in an NADPH-generating
Kannan Vivekanandan et al.
Rapid communications in mass spectrometry : RCM, 20(11), 1731-1735 (2006-05-06)
A strategy is developed for the identification of isocephalomannine in the presence of alkali metal ion adducts and other cephalomannine isomers in a paclitaxel active pharmaceutical ingredient. Intact molecular ion analyses and a sub-structural study have been performed for the
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