{N-[(2R,3S,5S,6R)-5-amino-2-methyl-6-{[(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]carbamimidoyl}formic acid hydrochloride

• ChemBase ID: 153749
• Molecular Formular: C14H26ClN3O9
• Molecular Mass: 415.82394
• Monoisotopic Mass: 415.13575711
• SMILES: C[C@@H]1[C@H](C[C@@H]([C@H](O1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H]([C@@H]1O)O)O)O)O)N)NC(=N)C(=O)O.Cl
• Canonical SMILES: N[C@H]1C[C@H](NC(=N)C(=O)O)[C@H](O[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@@H]([C@@H]([C@H]1O)O)O)C.Cl
• InChI: InChI=1S/C14H25N3O9.ClH/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);1H/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-;/m1./s1
• InChIKey: ZDRBJJNXJOSCLR-NZXABURVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {N-[(2R,3S,5S,6R)-5-amino-2-methyl-6-{[(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}oxan-3-yl]carbamimidoyl}formic acid hydrochloride
• IUPAC Traditional name: kasugamycin hydrochloride
• Synonyms: 3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-D-arabino-hexopyranosyl]-D-chiro-inositol; Kasugamycin hydrochloride from Streptomyces kasugaensis

Database IDs

• CAS Number: 19408-46-9
• MDL Number: MFCD00058459
• PubChem SID: 162247888; 24896238
• PubChem CID: 88045

CALCULATED PROPERTIES

• Acid pKa: 2.868796
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -6.4029083
• LogD (pH = 7.4): -6.4303517
• Log P: -6.394792
• Molar Refractivity: 92.5732 cm^3
• Polarizability: 33.85296 Å^3
• Polar Surface Area: 218.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble

Safety Information

• RTECS: NM7521800
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C14H25N3O9 · HCl

DETAILS

Sigma Aldrich - K4013

Application
Kasugamycin (Ksg) is an aminoglycoside antibiotic isolated from Streptomyces kasugaensis. It is used to study ribosome structure and interactions near the m26A m26A sequence1. It is used to study the mechanisms of kasugamycin resistance2.
Biochem/physiol Actions
kasugamycin binds within the mRNA channel of the 30S subunit between the universally conserved G926 and A794 nucleotides in 16S ribosomal RNA2. Inhibits protein synthesis and binding of aminoacyl-SRNA to the ribosomes in fungi. Induces f-met-tRNA dissociation from P-site of 30S subunit.