Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2020-02-26 21:40:00 UTC |
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HMDB ID | HMDB0014622 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Amikacin |
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Description | Amikacin is a semi-synthetic aminoglycoside antibiotic derived from kanamycin A. Similar to other aminoglycosides, amikacin disrupts bacterial protein synthesis by binding to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and tRNA acceptor sites leading to the production of non-functional or toxic peptides. Other mechanisms not fully understood may confer the bactericidal effects of amikacin. Amikacin is also nephrotoxic and ototoxic. |
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Structure | |
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Synonyms | Value | Source |
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1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin a | ChEBI | Amicacin | ChEBI | Amiglyde-V | ChEBI | Amikacina | ChEBI | Amikacine | ChEBI | Amikacinum | ChEBI | Amikavet | ChEBI | Briclin | ChEBI | O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine | ChEBI | AMK | Kegg | 1-N-(L(-)-g-Amino-a-hydroxybutyryl)kanamycin a | Generator | 1-N-(L(-)-Γ-amino-α-hydroxybutyryl)kanamycin a | Generator | O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-a-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine | Generator | O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-α-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine | Generator | Amikacin base | HMDB | Amikacin dihydrate | HMDB | Amikacin sulfate | HMDB | ANTIBIOTIC BB-K8 | HMDB | BB-K8 | HMDB | A.M.K | HMDB | Amikacina normon | HMDB | Amikafur | HMDB | Amikason's | HMDB | Amikin | HMDB | Bristol myers squibb brand OF amikacin sulfate | HMDB | Bristol-myers squibb brand OF amikacin sulfate | HMDB | Collins brand OF amikacin sulfate | HMDB | Fustery brand OF amikacin sulfate | HMDB | Galen brand OF amikacin sulfate | HMDB | Gamikal | HMDB | Medical, amikacina | HMDB | Normon, amikacina | HMDB | Son's brand OF amikacin sulfate | HMDB | Sulfate, amikacin | HMDB | Amikacina medical | HMDB | Amikalem | HMDB | Amiklin | HMDB | Apothecon brand OF amikacin sulfate | HMDB | BB K 8 | HMDB | BB-K 8 | HMDB | BBK 8 | HMDB | Norman brand OF amikacin sulfate | HMDB | Amikayect | HMDB | Amukin | HMDB | BBK8 | HMDB | Biclin | HMDB | Biklin | HMDB | Cryopharma brand OF amikacin sulfate | HMDB | Grossmann brand OF amikacin sulfate | HMDB | Kanbine | HMDB | Lemery brand OF amikacin sulfate | HMDB | Mead johnson brand OF amikacin sulfate | HMDB | Yectamid | HMDB | BB K8 | HMDB | Medical brand OF amikacin sulfate | HMDB | Oprad | HMDB | Pisa brand OF amikacin sulfate | HMDB | Rovi brand OF amikacin sulfate | HMDB |
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Chemical Formula | C22H43N5O13 |
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Average Molecular Weight | 585.6025 |
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Monoisotopic Molecular Weight | 585.285736487 |
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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 |
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Traditional Name | amikacin |
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CAS Registry Number | 37517-28-5 |
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SMILES | NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O |
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InChI Identifier | InChI=1S/C22H43N5O13/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)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1 |
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InChI Key | LKCWBDHBTVXHDL-RMDFUYIESA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | 4,6-disubstituted 2-deoxystreptamines |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 203 - 204 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 49.7 g/L | Not Available | LogP | -7.4 | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0hh9-9803480000-4e62c20842f82ac0dc88 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-001i-9400112000-f033c515f4f33f591c6d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0arr-0012930000-e9e5c2d0a10606a482a9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08fr-1172910000-aa60237b3c5b04a8a3e9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03k9-4589400000-6018610d9123baec32bf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0089-3804890000-fcfb985392039be545de | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dl-7323930000-388eeb644330ca9e4545 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0229-9787300000-fe9d1c5ff399b6290a43 | Spectrum |
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