Basic information
- CAS
11030-24-3- 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- InChIKey
PVTHJAPFENJVNC-RKODIXKRNA-N- Molecular formula
- C14H25N3O9
- Average molar mass
- 379.36 g/mol
- Monoisotopic mass
- 379.15907938
Overview
Kasugamycin is an amino cyclitol glycoside that is isolated from Streptomyces kasugaensis and exhibits antibiotic and fungicidal properties. It has a role as a protein synthesis inhibitor, a bacterial metabolite and an antifungal agrochemical. It is an amino cyclitol glycoside, an aminoglycoside antibiotic, a carboxamidine, a monosaccharide derivative and an antibiotic fungicide.
Names & identifiers
- Preferred name
- Einecs 234-260-3
- 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
- English name
- KASUGAMYCIN
- Molecular formula
- C14H25N3O9
- Molecular weight
- 379.36
Names & synonyms
EINECS 234-260-3RefChem:1084063KASUGAMYCIN6980-18-3Kasumin LKasumin 2LKasu BKasuminlNSC 100858O957UYB9DY2-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 acid11030-24-3
Show more names
2-(((2R,3S,5S,6R)-5-Amino-2-methyl-6-(((1R,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)amino)-2-iminoacetic acidKasugamycin 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-chiroinoxitolharumycinα-D-lyxo-Brn 140382360%Kasugamycinkasumin-bordeaux
(1s,2r,3s,4r,5s,6s)-2,3,4,5,6-Pentahydroxycyclohexyl 2-Amino-4-{[carboxy(Imino)methyl]amino}-2,3,4,6-Tetradeoxy-Alpha-D-Arabino-Hexopyranoside3-O-(2-Amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl)-D-chiro-inositol sulphateKSM2-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 acid3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl]-D-chiro-inositolD-chiro-Inositol, 3-O-(2-amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl)-HSDB 6695C14H25N3O9
Properties
Computed structural properties
- XLogP
- -6.7
- Topological polar surface area
- 221 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 532
Experimental & physicochemical properties
Collision Cross Section
165.9 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2040739]
185.39 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Boiling point
- 507.24 °C · 507.24°C (rough estimate)
- Density
- 1.2554 · 1.2554 (rough estimate)
- refractive index
- 1.57 · 1.5700 (estimate)
- solubility
- Aqueous Base (Slightly), Water (Slightly)
- form
- Solid
- pka
- -0.62 · -0.62±0.41(Predicted)
- color
- Pale Yellow to Pale Beige
- 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 · 6980-18-3
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
- Hazardous Substances Data
- 6980-18-3(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionTrade 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.
UsesKasugamycin is an antibiotic aminoglycoside that inhibits protein synthesis.
General DescriptionKasugamycin 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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
山东海舟生物工程有限公司
Related reactions
0 records
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Compound notes
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