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Key Documents

C4991

Sigma-Aldrich

Cephalomannine

≥97% (HPLC), solid

Synonym(s):

NSC 318735

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About This Item

Empirical Formula (Hill Notation):
C45H53NO14
CAS Number:
Molecular Weight:
831.90
MDL number:
UNSPSC Code:
12352200
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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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 a taxol derivative with antitumor, antiproliferative properties.
Cephalomannine is isolated from Taxus wallichiana, and serves as an antifungal agent.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
S H Sheikh et al.
Analytical biochemistry, 283(1), 33-38 (2000-08-10)
A new fluorescence immunoassay for the quantitative determination of paclitaxel (Pac) under equilibrium conditions was developed. Anti-Pac IgG2a antibody was immobilized through its Fc region to protein A covalently bound to the inside surface of a silanized glass capillary column
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
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

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