Apramycin sulfate salt - analytical standard , CAS No.65710-07-8

CAS: 65710-07-8 Cat. No.: A106706 Molecular Weight: 637.66 EC Number: 265-890-7 PubChem CID: 3081544

GRADE & PURITY Analytical standard

Synonyms

Apramycin Sulfate, Antibiotic for Culture Media Use Only | W-104790 | (2R,3R,4S,5S,6S)-5-amino-2-(((2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl)oxy

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

Apramycin Sulfate, Antibiotic for Culture Media Use Only | W-104790 | (2R, 3R, 4S, 5S, 6S)-5-amino-2-(((2R, 3S, 4R, 4aR, 6S, 7R, 8aS)-7-amino-6-(((1R, 2R, 3S, 4R, 6S)-4, 6-diamino-2, 3-dihydroxycyclohexyl)oxy)-4-hydroxy-3-(methylamino)octahydropyrano[3, 2-b]pyran-2-yl)oxy

Specifications & Purity

analytical standard

Biochemical and Physiological Mechanisms

Aminoglycoside antibiotic agent. Potent protein synthesis inhibitor. Inhibits translocation. Shows bactericidal effects in vivo. Orally active.

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Analytical standard

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

• Canonical Smiles: CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O.OS(=O)(=O)O
• IUPAC Name: (2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol;sulfuric acid
• InChIKey: WGLYHYWDYPSNPF-RQFIXDHTSA-N
• INCHI: 1S/C21H41N5O11.H2O4S/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1
• Isomeric SMILES: CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O.OS(=O)(=O)O
• WGK Germany: 3
• Alternate CAS: 37321-09-8
• PubChem CID: 3081544
• Molecular Weight: 637.66

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

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Aminoglycosides
• Direct Parent: Aminocyclitol glycosides
• Alternative Parents: Hexoses Aminocyclitols and derivatives Cyclohexanols Cyclohexylamines Oxanes Organic sulfuric acids 1,3-aminoalcohols 1,2-aminoalcohols Oxacyclic compounds Acetals Dialkylamines Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Amino cyclitol glycoside - Hexose monosaccharide - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Sulfuric acid - Cyclitol or derivatives - Monosaccharide - Oxane - Organic sulfuric acid or derivatives - 1,3-aminoalcohol - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Secondary amine - Acetal - Organoheterocyclic compound - Oxacycle - Secondary aliphatic amine - Primary alcohol - Organic oxide - Hydrocarbon derivative - Primary aliphatic amine - Organopnictogen compound - Organic nitrogen compound - Amine - Alcohol - Primary amine - Organonitrogen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
• 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

Chemical and Physical Properties

• Flash Point(°F): 230°F
• Flash Point(°C): >110℃
• Boil Point(°C): 823℃
• Melt Point(°C): 168℃
• Molecular Weight: 637.700 g/mol
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 6
• Exact Mass: 637.248 Da
• Monoisotopic Mass: 637.248 Da
• Topological Polar Surface Area: 367.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 841.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 17
• 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

References

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6. Haohao Chen, Min Yuan, Fengqin Yin, Hui Cao, Xiuxiu Wu, Liling Hao, Weiyan Shi, Tai Ye, Fei Xu.  (2025)  Freezing-driven assembly of DNA walking machine facilitate G4 nanowires growth for electrochemical detection of kanamycin.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.113237]

7. Tingting Wang, Huaizhi Yang, Qiushuang Sheng, Ying Ding, Jian Zhang, Feng Chen, Jianfeng Wang, Lei Song, Xuming Deng.  (2025)  Isoferulic acid facilitates effective clearance of hypervirulent Klebsiella pneumoniae through targeting capsule.  PLoS Pathogens,  21  (1): (e1012787).  [PMID:39761301] [10.1371/journal.ppat.1012787]

8. Lihua Yang, Hang Zhai, Tingting Tian, Botong Liu, Xianpu Ni, Huanzhang Xia*.  (2025)  Combinatorial biosynthesis of novel gentamicin derivatives with nonsense mutation readthrough activity and low cytotoxicity.  Frontiers in Pharmacology,      [PMID:40342992] [10.3389/fphar.2025.1575840]

9. Huanhuan Zhang, Fengjun Sun, Wei Feng, Yan Qian.  (2025)  Polymyxin B combined with amikacin delays the resistance of Klebsiella pneumoniae to polymyxin B by modulating the expression of NlpE.  INFECTION GENETICS AND EVOLUTION,      [PMID:40480594] [10.1016/j.meegid.2025.105780]

10. Haobo Xing, Qingming Hou, Zhenhua Wang, Shanfei Zhang, Shangxia Song, Lulu Du, Chenghua Gao, Yunfei Li, Fubao Sun.  (2026)  Enhanced Monensin Biosynthesis in Streptomyces cinnamonensis with Multigene Integration and Overexpression of Newly Identified Genes.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2026.110118]