| Identification | Back Directory | [Name]
KASUGAMYCIN | [CAS]
6980-18-3 | [Synonyms]
kasuminl
Hsdb 6695
Brn 1403823
KASUGAMYCIN
kasumin-bordeaux
Kasugamycin base
78822-08-9 (Sulfate salt)
KASUGAMYCIN HYDROCHLORIDE 80%
19408-46-9 (Mono-hydrochloride)
-alpha-d-arabino-hexopyranosyl)-
11030-24-3 (Unspecified sulfate salt)
101651-86-9 (Unspecified phosphate salt)
[5-amino-2-methyl-6-(2,3,4,5,6-pentahydroxycyclohexyloxy0 pyran-3-yl] amino-α-iminoacetic acid
3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-.alpha.-D-arabinobexopyranosyl-D-chiro-inositol
3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-.alpha.-D-arabinobexopyranosyl-D-chiro-inositol
D-Chiro-inositol, 3-o-(2-amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl)-
Kasugamycin 3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-.alpha.-D-arabinobexopyranosyl-D-chiro-inositol kasuminl 3-O-[2-Amino-4-[(carboxyiminomethyl)amino]2,3,4,6-tetradeoxy-1-D-arabinohexopyranosyl]-D-chiroinoxitol | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C14H25N3O9 | [MDL Number]
MFCD00136694 | [MOL File]
6980-18-3.mol | [Molecular Weight]
379.36 |
| Chemical Properties | Back Directory | [Boiling point ]
507.24°C (rough estimate) | [density ]
1.2554 (rough estimate) | [refractive index ]
1.5700 (estimate) | [solubility ]
Aqueous Base (Slightly), Water (Slightly) | [form ]
Solid | [pka]
-0.62±0.41(Predicted) | [color ]
Pale Yellow to Pale Beige | [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-/s3 | [InChIKey]
PVTHJAPFENJVNC-RKODIXKRNA-N | [SMILES]
O=C(C(=N)N[C@H]1C[C@H](N)[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H]1C)O |&1:5,7,9,11,12,14,16,18,20,23,r| | [CAS DataBase Reference]
6980-18-3 | [EPA Substance Registry System]
Kasugamycin (6980-18-3) |
| Hazard Information | Back Directory | [Definition]
ChEBI: An amino cyclitol glycoside that is isolated from Streptomyces kasugaensis and exhibits antibiotic and fungicidal properties. | [Description]
Trade names: “Kasugamin,” “Kasumin” Patent: JP
42006818; BE 657659: GB 1094566. Systemic fungicide
and bactericide with protective and curative action.
Controls rice blast caused by Pyricularia oryzae and
other rice diseases, such as bacterial grain rot, bacterial
seedling blight, and bacterial brown stripe caused
by Pseudomonas spp. (15). Effective on other plant diseases,
e.g., leaf mold and bacterial canker in tomatoes,
bean halo blight, scab on apples, Cercospora spp. leaf
spot on sugar beet, and bacterial soft rot on potatoes. | [Chemical Properties]
Its hydrochloride appears as white needle-shaped or flaky crystals. Its mp is 206-210°C (202-204°C, 236-239°C). It is insoluble in many organic solvents, including methanol, ethanol, propanol, and benzene, but readily soluble in water. It is relatively stable in acidic or neutral media but easily destroyed by alkali. At a pH of 5, its potency did not decrease after storage at 50°C for 10 weeks, but at a pH of 9, its potency dropped to 42.6%. | [Uses]
Kasugamycin is an antibiotic aminoglycoside that inhibits protein synthesis. | [General Description]
Kasugamycin was found in the culture broth of Streptomyces kasugaensis by Umezawa et al. in 1965. It has an aminocyclitol structure and shows strong activity against phytopathogenic fungi, especially Pericularia oryzae, the pathogen causing rice blast. This drug also shows activity against Pseudomonas, and its toxicity is very low; no mice died following intravenous injection of doses as high as two grams per kilogram. Kasugamycin has been used to protect rice plants against rice blast and for animal infections. | [Toxicity evaluation]
Nonphytotoxic to rice, tomatoes, sugar beet, potatoes,
and other vegetables, but slightly toxic to peas, beans,
grapes, citrus, and apples. |
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