Amikacin hydrate - aminoglycoside antibiotic , CAS No.1257517-67-1

CAS: 1257517-67-1 Cat. No.: A475881 Molecular Weight: 585.6(Anhydrous)

GRADE & PURITY aminoglycoside antibiotic

Synonyms

MLS002207279 | SMR001306795 | Amikacin hydrate 100 microg/mL in Acetonitrile/Water | cid_16218899 | (S)-4-Amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(a

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Chemical structure: aminoglycosideAmikacin hydrate is used in antimicrobial susceptibility studies of organisms such asMycobacterium tuberculosisandEhrlichia phagocytophila.

Specifications

Synonyms

MLS002207279 | SMR001306795 | Amikacin hydrate 100 microg/mL in Acetonitrile/Water | cid_16218899 | (S)-4-Amino-N-((1R, 2S, 3S, 4R, 5S)-5-amino-2-(((2S, 3R, 4S, 5S, 6R)-4-amino-3, 5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R, 3R, 4S, 5S, 6R)-6-(a

Specifications & Purity

aminoglycoside antibiotic

Biochemical and Physiological Mechanisms

Amikacin inhibits bacterial protein synthesis by binding to the 30S ribosome subunit and inducing mRNA misreading. It interferes with the translocation of tRNA from the A-site to the P-site.

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Note

Keep container tightly closed in a dry and well-ventilated place.

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.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;hydrate
• InChIKey: DTSOZYYWEZJFSS-XTHCGPPUSA-N
• INCHI: 1S/C22H43N5O13.H2O/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;/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);1H2/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.O
• Alternate CAS: 37517-28-5
• Molecular Weight: 585.6(Anhydrous)
• Reaxy-Rn: 37256523
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37256523&ln=

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: Gamma amino acids and derivatives O-glycosyl compounds Aminocyclitols and derivatives Cyclohexanols Cyclohexylamines Oxanes Monosaccharides N-acyl amines 1,3-aminoalcohols 1,2-aminoalcohols Secondary carboxylic acid amides Acetals Polyols Oxacyclic compounds Monoalkylamines Hydrocarbon derivatives Primary alcohols Carbonyl compounds Organic oxides Organopnictogen compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 4,6-disubstituted 2-deoxystreptamine - Gamma amino acid or derivatives - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Fatty acyl - Monosaccharide - N-acyl-amine - Cyclitol or derivatives - Fatty amide - Oxane - 1,3-aminoalcohol - Cyclic alcohol - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Amino acid or derivatives - 1,2-aminoalcohol - Carboxylic acid derivative - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Carbonyl group - Primary alcohol - Primary amine - Hydrocarbon derivative - Amine - Alcohol - Organic oxide - Organopnictogen compound - 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: Not available

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(Human)

RACGAP1 Tbio Rac GTPase-activating protein 1 (2057 Activities)

Discover Target: RACGAP1

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

RAD52 Tchem DNA repair protein RAD52 homolog (856 Activities)

Discover Target: RAD52

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

CRHR2 Tchem Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein (4148 Activities)

Discover Target: CRHR2

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Escherichia coli (133304 Activities)

Explore this target

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 603.600 g/mol
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 10
• Exact Mass: 603.296 Da
• Monoisotopic Mass: 603.296 Da
• Topological Polar Surface Area: 333.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 819.000
• 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: 2

XLogP3