Kasugamycin hydrochloride
Basic information
- CAS
19408-46-9- Standard SMILES
C[C@H]1O[C@H](OC2[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]2O)[C@@H](N)C[C@@H]1N=C(N)C(=O)O.Cl- InChIKey
ZDRBJJNXJOSCLR-MFACZBEDNA-N- Molecular formula
- C14H26ClN3O9
- Average molar mass
- 415.82 g/mol
- Monoisotopic mass
- 415.1357571
Overview
See also: Kasugamycin hydrochloride (annotation moved to) ... View More ...
Names & identifiers
- Preferred name
- Kasugamycin hydrochloride
- IUPAC
- 2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid;hydrochloride
- English name
- Kasugamycin hydrochloride
- Molecular formula
- C14H25N3O9.ClH
- Molecular weight
- 415.82
Names & synonyms
Kasugamycin hydrochloride19408-46-9KasuminKasugamycin HClKasugamycin, monohydrochlorideKasugamycin monohydrochlorideDTXSID2040739MFCD00058459SXA18D440T2-(((2R,3S,5S,6R)-5-Amino-2-methyl-6-(((1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)amino)-2-iminoacetic acid hydrochlorideKasugamycin (hydrochloride)2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2S,3S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid;hydrochloride
Show more names
Kasugamycin hykasugamycin (jmaff)KASUGAMYCIN HYDROCHLKASUGAMYCIN HCL HYDRATEKsugamycinhydrochlorideKasugamycin HCl, Monohydratekasugamycin,monohydrochloride
D-chiro-Inositol,3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-a-D-arabino-hexopyranosyl]-, monohydrochlorideC14H26ClN3O9D-chiro-Inositol, 3-O-(2-amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl)-, monohydrochlorideUNII-SXA18D440TSR-05000001429Ksg hydrochlorideD-chiro-Inositol, 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-a-D-arabino-hexopyranosyl]-, monohydrochloride (9CI); Kasugamycin, monohydrochloride (8CI); Kasugamycin hydrochloride; KasuminD-chiro-Inositol, 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl]-, monohydrochloride
Properties
Computed structural properties
- Topological polar surface area
- 221 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 532
Experimental & physicochemical properties
Collision Cross Section185.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 202 · 202-204 °C (decomp)
- vapor pressure
- -8 Pa · -8 Pa (25 °C)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 2 O: · H2O: soluble
- pka
- 3.23 · 3.23 (carboxyl), 7.73 and 11.0 (bases)
- Water Solubility
- 125 g · 125 g l-1 (25 °C)
- form
- Solid
- color
- white to off-white
- Stability
- Hygroscopic
- Major Application
- clinical testing
- InChIKey
- ZDRBJJNXJOSCLR-MFACZBEDNA-N
- SMILES
- O([C@H]1O[C@@H]([C@H](C[C@@H]1N)NC(=N)C(=O)O)C)[C@@H]1[C@H]([C@H]([C@@H]([C@@H]([C@H]1O)O)O)O)O.Cl |&1:1,3,4,6,15,16,17,18,19,20,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 2
- rtecs
- NM7521800
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H320-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionKasugamycin is an aminoglycosidic antibiotic isolated from S. kasugaensis. It blocks the initiation of translation, preventing initiation complex formation on 30S ribosomes in bacteria.
Usesantifungal
Useskasugamycin, derived from Streptomyces kasuguensis, is also used to control rice blast.It acts by inhibiting protein synthesis by interfering with the binding of aminoacyl-tRNA to the mRNA-30s ribosomal subunit complex (Yamaguchi, 1998).
UsesKasugamycin Hydrochloride is an aminoglycoside antibiotic that inhibits the initiation of translation. It is also a type of fungicide that controls leaf and neck blast disease caused by Pyricularia oryzae and increases rice yields.
Related reactions
3 records
Compound notes
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