Kendomycin

Names

[ Name ]:
Kendomycin

[Synonym ]:
(1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.1.0]tetracosa-2,5,7,14-tetraen-4-one
kendomycin from streptomyces violaceoruber
Kendomycin
1,19:5,9-Diepoxybenzocyclooctadecen-3(5H)-one, 6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-, (5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-

Biological Activity

[Description]:

Kendomycin ((−)-TAN 2162) is a polyketide antibiotic with remarkable antibacterial and cancer cells cytotoxic activities. Kendomycin tends to be bacteriostatic rather than bactericidal and inhibits the growth of the methicillin-resistant Staphylococcus aureus (MRSA) strain COL at a low concentration (MIC of 5 μg/mL). Kendomycin is a potent antagonist of the endothelin receptor and a calcitonin receptor agonist which plays its role as an anti-osteoporotic agent[1][2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> CGRP Receptor

Research Areas >> Cancer

Signaling Pathways >> Neuronal Signaling >> CGRP Receptor

Research Areas >> Infection

Signaling Pathways >> GPCR/G Protein >> Endothelin Receptor

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Yasser A Elnakady, et al. Investigations to the Antibacterial Mechanism of Action of Kendomycin. PLoS One. 2016 Jan 21;11(1):e0146165.

[2]. Yu Yuan, et al. Total synthesis of kendomycin: a macro-C-glycosidation approach. J Am Chem Soc. 2004 Nov 17;126(45):14720-1.

[3]. Tetsuya Sengoku, et al. Total synthesis of the antibiotic kendomycin: a macrocyclization using the Tsuji-Trost etherification. Angew Chem Int Ed Engl. 2014 Apr 14;53(16):4213-6.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
678.5±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₉H₄₂O₆

[ Molecular Weight ]:
486.640

[ Flash Point ]:
219.9±25.0 °C

[ Exact Mass ]:
486.298126

[ PSA ]:
96.22000

[ LogP ]:
5.94

[ Vapour Pressure ]:
0.0±4.7 mmHg at 25°C

[ Index of Refraction ]:
1.576

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Structure and biosynthesis of kendomycin, a carboxylic ansa-compound from Streptomyces. . Zeeck, A. , and Bode, H.B.

J. Chem. Soc. Perkin Trans. I , 323, (2000)

Related Compounds

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