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Kasugamycin

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Name

Kasugamycin

EINECS
CAS No. 6980-18-3 Density 1.97 g/cm3
Solubility Melting Point 203oC (dec)
Formula C14H25N3O9 Boiling Point 585.9 °C at 760 mmHg
Molecular Weight 379.42 Flash Point 308.2 °C
Transport Information Appearance
Safety Risk Codes
Molecular Structure Molecular Structure of 6980-18-3 (D-chiro-Inositol,3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-a-D-arabino-hexopyranosyl]-) Hazard Symbols
Synonyms

Kasugamycin(8CI);KSM;Kasu B;Kasumin 2L;Kasumin L;α-D-arabino-hexopyranoside, (1α,2β,3α,4α,5β,6β)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-;3-O-(2-Amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-a-D-arabino-hexopyranosyl)-D-chiro-inositol;(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-{[carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside;(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-Pentahydroxycyclohexyl-2-amino-4-{[carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside;

 

Kasugamycin Consensus Reports

Reported in EPA TSCA Inventory.

Kasugamycin Specification

The Kasugamycin, with the CAS registry number 6980-18-3, has the systematic name of (1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-{[carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-α-D-lyxo-hexopyranoside. It is an aminoglycoside antibiotic. And the molecular formula of this chemical is C14H25N3O9.

The physical properties of Kasugamycin are as following: (1)# of Rule of 5 Violations: 2; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 12; (7)#H bond donors: 10; (8)#Freely Rotating Bonds: 10; (9)Polar Surface Area: 218.81 Å2; (10)Index of Refraction: 1.738; (11)Molar Refractivity: 77.4 cm3; (12)Molar Volume: 192.2 cm3; (13)Polarizability: 30.68×10-24cm3; (14)Surface Tension: 88.5 dyne/cm; (15)Density: 1.97 g/cm3; (16)Flash Point: 308.2 °C; (17)Enthalpy of Vaporization: 100.47 kJ/mol; (18)Boiling Point: 585.9 °C at 760 mmHg; (19)Vapour Pressure: 3.6E-16 mmHg at 25°C.

Preparation of Kasugamycin: It is the metabolite of Actinomycetes microaurous. And can be obtained by the pure liquid submerged fermentation using soybean cake meal, malt extract, seed fat and dusty yeast as raw materials.

Uses of Kasugamycin: It is a kind of antibiotic both used in agriculture and medicina, and has a effective inhibition to Magnaporthe grisea. Besides, it is also used for the control of anthrax in cucumber and broomcorn, and leaf mold in tomato. In addition, it is used in pseudomonas infections, and interfers with protein synthesis in susceptible Escherichia coli.

You can still convert the following datas into molecular structure:
(1)SMILES: OC(=O)C(=N)N[C@H]2C[C@H](N)[C@@H](O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O)O[C@@H]2C
(2)InChI: InChI=1/C14H25N3O9/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24)/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-/m1/s1
(3)InChIKey: PVTHJAPFENJVNC-MHRBZPPQBX

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 21gm/kg (21000mg/kg)   Pesticide Manual. Vol. 9, Pg. 515, 1991.
mouse LD50 skin > 10gm/kg (10000mg/kg)   Pesticide Manual. Vol. 9, Pg. 515, 1991.
quail LD50 oral > 4gm/kg (4000mg/kg)   Pesticide Manual. Vol. 9, Pg. 515, 1991.
rat LD50 oral 11400mg/kg (11400mg/kg)   Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
rat LD50 skin > 4gm/kg (4000mg/kg)   Pesticide Manual. Vol. 9, Pg. 515, 1991.

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