Amikacin disulfate - Moligand™,10mM in Water , Bacterial 70S ribosome inhibitor, CAS No.39831-55-5, Bacterial 70S ribosome inhibitor

CAS: 39831-55-5 Cat. No.: A423830 Molecular Weight: 781.76 Beilstein Registry Number: 6172633 EC Number: 254-648-6 PubChem CID: 38351

GRADE & PURITY Moligand™, 10mM in Water

Synonyms

Chemacin | O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-6))-N(sup 3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine sulfate (1:2) | Amikacin sulfate, United States Pharmacopeia (USP) Reference Standard |

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Amikacin sulfate binds to 16S rRNA (bacterial 30S ribosome), causing misreading of mRNA and supressing proteins synthesis.
An aminoglycoside antibiotic that is active against gram-negative bacteria

Specifications

Synonyms

Chemacin | O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-6))-N(sup 3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine sulfate (1:2) | Amikacin sulfate, United States Pharmacopeia (USP) Reference Standard |

Specifications & Purity

Moligand™, 10mM in Water

Biochemical and Physiological Mechanisms

Amikacin disulfate, also known as BB-K 8, is an aminoglycoside antibiotic that is active against gram-negative bacteria. The activity of Amikacin is similar to that of Kanamycin and Gentamicin. Amikacin has been used in different types of renal studies. W

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Bacterial 70S ribosome inhibitor

Names and Identifiers

• Canonical Smiles: C1C(C(C(C(C1NC(=O)C(CCN)O)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)O)N.OS(=O)(=O)O.OS(=O)(=O)O
• IUPAC Name: (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide;sulfuric acid
• InChIKey: FXKSEJFHKVNEFI-GCZBSULCSA-N
• INCHI: 1S/C22H43N5O13.2H2O4S/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21;2*1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);2*(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;;/m0../s1
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCN)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N.OS(=O)(=O)O.OS(=O)(=O)O
• Alternate CAS: 37517-28-5
• PubChem CID: 38351
• Molecular Weight: 781.76
• Beilstein: 6172633

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides
            • Level7 Aminocyclitol glycosides
              • Level8 2-deoxystreptamine aminoglycosides
                • Level9 4,6-disubstituted 2-deoxystreptamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Aminoglycosides - Aminocyclitol glycosides - 2-deoxystreptamine aminoglycosides
• Direct Parent: 4,6-disubstituted 2-deoxystreptamines
• Alternative Parents: O-glycosyl compounds Aminocyclitols and derivatives Cyclohexanols Cyclohexylamines Oxanes Organic sulfuric acids Monosaccharides 1,3-aminoalcohols 1,2-aminoalcohols Propargyl-type 1,3-dipolar organic compounds Acetals Polyols Carboximidic acids Oxacyclic compounds Primary alcohols Organopnictogen compounds Hydrocarbon derivatives Monoalkylamines Organic oxides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 4,6-disubstituted 2-deoxystreptamine - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Sulfuric acid - Oxane - Cyclitol or derivatives - Monosaccharide - Organic sulfuric acid or derivatives - Cyclic alcohol - 1,3-aminoalcohol - Secondary alcohol - 1,2-aminoalcohol - Propargyl-type 1,3-dipolar organic compound - Oxacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Polyol - Acetal - Carboximidic acid - Carboximidic acid derivative - Hydrocarbon derivative - Organopnictogen compound - Primary aliphatic amine - Organic oxide - Organonitrogen compound - Organic nitrogen compound - Amine - Alcohol - Primary alcohol - Primary amine - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
• External Descriptors: aminoglycoside sulfate salt

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Pseudomonas fluorescens (1630 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Sensitive to humidity and heat
• Specific Rotation[α]: +76.0 to +84.0 deg(C=1, water)(calcd.onanh.substance)
• Melt Point(°C): 220-230°C
• Molecular Weight: 781.800 g/mol
• Hydrogen Bond Donor Count: 17
• Hydrogen Bond Acceptor Count: 25
• Rotatable Bond Count: 10
• Exact Mass: 781.22 Da
• Monoisotopic Mass: 781.22 Da
• Topological Polar Surface Area: 498.000 Ų
• Heavy Atom Count: 50
• Formal Charge: 0
• Complexity: 900.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 16
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

References

1. Lu Qi, Shanshan Liu, Zhen Yan, Min Qiao, Haonan Peng, Liping Ding.  (2023)  A cross-reactive fluorescent ensemble based on perylene derivative/surfactant assemblies for discrimination of multiple aminoglycoside antibiotics in aqueous solution.  JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY,      [PMID:] [10.1016/j.jphotochem.2023.115128]

2. Ye Hua, Wan Tianxiang, Li Xinfu, Li Chao, He Kuo, Guo Yuanxin.  (2022)  Rapid detection of kanamycin using cooperative recognition split aptamer and graphene oxide nanosheets.  Journal of Food Measurement and Characterization,      [PMID:] [10.1007/s11694-022-01781-9]

3. Zhaojie Wang, Yuanhao Qiu, Chunyan Hou, Dongdong Wang, Feifei Sun, Xiaojun Li, Feng Wang, Hong Yi, Haibo Mu, Jinyou Duan.  (2017)  Synthesis of hyaluronan-amikacin conjugate and its bactericidal activity against intracellular bacteria in vitro and in vivo.  CARBOHYDRATE POLYMERS,      [PMID:29253955] [10.1016/j.carbpol.2017.10.061]

4. Xu Zuo, Xiaoping Guo, Dan Zhao, Yinuo Gu, Zheng Zou, Yuanyuan Shen, Chaoliang He, Caina Xu, Yan Rong, Fang Wang.  (2024)  An antibacterial, multifunctional nanogel for efficient treatment of neutrophilic asthma.  JOURNAL OF CONTROLLED RELEASE,      [PMID:38866241] [10.1016/j.jconrel.2024.06.024]

5. Guo Xiaoping, Zuo Xu, Zheng Wenxue, Zhao Dan, Dong Chao, Zou Zheng, Shen Yuanyuan, Xu Caina, He Chaoliang, Wang Fang.  (2025)  Catalase-encapsulated matrix metalloproteinase-9 responsive nanogels for modulation of inflammatory response and treatment of neutrophilic asthma.  JOURNAL OF NANOBIOTECHNOLOGY,  23  (1): (1-17).  [PMID:40410884] [10.1186/s12951-025-03470-3]