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Kanamycin

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Identification
Molecular formula
C18H36N4O11
CAS number
59-01-8
IUPAC name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol
State
State

Kanamycin is generally found in a solid state at room temperature.

Melting point (Celsius)
270.00
Melting point (Kelvin)
543.00
Boiling point (Celsius)
269.00
Boiling point (Kelvin)
542.00
General information
Molecular weight
484.55g/mol
Molar mass
484.5460g/mol
Density
1.6800g/cm3
Appearence

Kanamycin appears as a white to off-white powder. It is typically crystalline and hygroscopic in nature.

Comment on solubility

Solubility of (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol

The solubility of this compound is influenced by its complex structure, which comprises multiple functional groups. In general, the following points regarding its solubility should be considered:

  • Hydrophilicity: Due to the presence of numerous hydroxyl (-OH) and amino (-NH2) groups, the compound exhibits significant hydrophilic characteristics, suggesting that it will be soluble in polar solvents such as water.
  • Hydrophobic Regions: Certain sections of its structure may introduce hydrophobic characteristics, which could lead to variability in solubility depending on the solvent used.
  • pH Sensitivity: The solubility of this compound may vary with pH, particularly because of the amino groups that can protonate or deprotonate, enhancing solubility in acidic or basic conditions.
  • Conformational Considerations: The stereochemical complexity and specific conformation of the compound can also play a role in its solubility, potentially affecting interactions with solvents.

In conclusion, while the compound is expected to exhibit a degree of solubility in polar solvents due to its hydrophilic features, variances in structural factors and environmental conditions can significantly influence its overall solubility behavior. Understanding these nuances is critical for its application in various chemical and biological contexts.

Interesting facts

Exploring the Unique Compound: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol

This compound presents a fascinating study in chirality and molecular complexity, showcasing how small changes in structure can lead to significant differences in biological activity. Here are some key points to consider:

  • Chirality: The compound contains multiple chiral centers, indicating that it can exist in different stereoisomeric forms. Each stereoisomer may exhibit unique biochemical behavior, making chirality an important factor in pharmacology and biochemistry.
  • Biological Relevance: The presence of amino groups and dihydroxy structures suggests that this compound could play a role in various biological systems or may serve as a precursor in the synthesis of biologically active molecules.
  • Complexity: The intricate arrangement of multiple functional groups requires advanced synthetic methods for its production. Understanding its synthesis can highlight innovative techniques in current organic synthesis practices.
  • Potential Applications: Such complex molecules often find applications in the pharmaceutical industry, particularly as drug candidates or in the development of new therapies targeting specific diseases.
  • Structure-Activity Relationship (SAR): Studying this compound can provide insights into SAR, where the relationship between its chemical structure and biological activity is investigated, paving the way for drug design and optimization.

In conclusion, the unique structural features of this compound make it a compelling subject of study in chemistry and pharmacology. It emphasizes the importance of meticulous molecular design for achieving desired outcomes in chemical and biological systems. As students and scientists, we continually explore these complex molecules, expanding our knowledge and potentially enhancing therapeutic strategies.

Synonyms
Framycetin
neomycin
NEOMYCIN B
119-04-0
Fradiomycin
Mycifradin
Soframycin
Enterfram
Framygen
Actilin
Fradiomycin B
Framicetina
Framycetine
Neomas
Fradiomycinum
Framycetinum
1404-04-2
Neomycin B sulfate
Caswell No. 595
Nivemycin
NEOMYCIN SULFATE
Antibiotic 10676
Neobrettin
USAF CB-19
CCRIS 5462
Framidal
Framycin
Francetin
Dekamycin iii
HSDB 3242
Soframycine
Actiline
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
Framycetin (INN)
Neomycin B Hexaacetate
Neo-Rx
Antibiotique
Myacyne
Neolate
ANTIBIOTIQUE EF 185
Neomycin sulphate
CHEBI:7508
Vonamycin powder V
Neomcin
Neomin
Neomycin Trisulfate Hydrate Deuterated
4BOC774388
(1R,2R,3S,4R,6S)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside
Neomicina [DCIT]
Fradiomycin Trisulfate Hydrate deuterated
Framycetinum [INN-Latin]
Neomicina
Neomycine
Neomycinum
PIMAVECORT
FRAMYCETIN [INN]
Neomycine [INN-French]
Neomycinum [INN-Latin]
Framycetine [INN-French]
NMY
Framicetina [INN-Spanish]
Framycetin [INN:BAN:DCF]
Bycomycin
Jernadex
11004-65-2
Fradiomycin B;Neomycin B
Neomycin [INN:BAN]
EINECS 204-292-2
EINECS 215-766-3
EPA Pesticide Chemical Code 006303
BRN 0101621
Mycerin
UNII-I16QD7X297
UNII-4BOC774388
Antibiotic 956
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol
Antibiotic produced by Streptomyces decaris. Neomycin B
NEOMYCIN B [MI]
Prestwick3_000158
Neomycin B; Fradiomycin B
SCHEMBL3279
FRAMYCETIN [WHO-DD]
BSPBio_000296
GTPL709
NEOMYCIN B [USP-RS]
4-18-00-07476 (Beilstein Handbook Reference)
D-Streptamine, O-2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1-4)-O-(O-2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl-(1-3)-beta-D-ribofuranosyl-(1-5))-2-deoxy-
BPBio1_000326
CHEMBL184618
DTXSID2023359
GLXC-10574
HMS2089P15
I16QD7X297
AKOS024284361
CS-6390
DB00452
NCGC00179612-01
D-Streptamine, O-2,6-diamino-2,6-dideoxy-.beta.-L-idopyranosyl-(1.->3)-O-.beta.-D-ribofuranosyl-(1->5)]-O-[2,6-diamino-2,6-dideoxy-.alpha.-D-glucopyranosyl-(1->4)]-2-deoxy
DA-63612
HY-17624
AB00443887
NS00072944
C01737
D05140
AB00443887-03
EN300-7480789
MYCIFRADIN; NEOMAS; PIMAVECORT; VONAMYCIN
ANTIBIOTIC PRODUCED BY STREPTOMYCES DECARIS
Q4492348
BRD-K71013094-001-02-5
BRD-K71013094-065-01-2
BRD-K71013094-326-01-8
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
(2S,3S,5R,6R)-5-amino-2-(aminomethyl)-6-(((2R,3S,4R,5S)-5-(((1R,2R,3S,5R,6S)-3,5-diamino-2-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-hydroxycyclohexyl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)tetrahydro-2H-pyran-3,4-diol
6-(2-{(4S,2R,3R,5R)-4-[(5S,6S,2R,3R,4R)-3-amino-6-(aminomethyl)-4,5-dihydroxy( 2H-3,4,5,6-tetrahydropyran-2-yloxy)]-3-hydroxy-5-(hydroxymethyl)oxolan-2-yloxy }(3S,6S,1R,2R,4R)-4,6-diamino-3-hydroxycyclohexyloxy)(3S,2R,4R,5R,6R)-5-amino- 2-(aminomethyl)-2H
D-STREPTAMINE, O-2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-.BETA.-D-RIBOFURANOSYL-(1->5))-2-DEOXY-
D-STREPTAMINE, O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-O-.BETA.-D-RIBOFURANOSYL-(1->5)-O-(2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXY-