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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Interactions between co-habitating fungi elicit synthesis of Taxol from an endophytic fungus in host Taxus plants
Soliman Sameh SM and Raizada MN
Frontiers in Microbiology, 4, 3-3 (2013)
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
Rui Sun et al.
Journal of separation science, 32(9), 1284-1293 (2009-04-11)
An environment-friendly method was established for the preparative separation and enrichment of four taxoids, namely 10-deacetylbaccatin III (10-DAB III), 7-xylosyl-10-deacetyltaxol (7-xyl-10-DAT), cephalomannine and paclitaxel from Taxus chinensis needles extracts. Characteristics of seven widely used macroporous resins for four taxoids were
K Glowniak et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 6(2), 135-140 (1999-06-22)
The concentrations of four common taxoids: baccatin III, paclitaxel, cephalomannine and 10-deacetylbaccatin III (10-DAB III) were measured in fresh needles and stems of Taxus baccata L. during the late autumn-spring period (November'96-April'97) which has not been investigated to date in

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