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Chemistry

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Also known as: Netilmicin sulfate, 56391-57-2, (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4-amino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol sulfate, Akos015961218, Ac-22349
Molecular Formula
C21H43N5O11S
Molecular Weight
573.7  g/mol
InChI Key
PQHZSWZPVGHDEZ-UIQTUGNFSA-N

Netilmicin
Semisynthetic 1-N-ethyl derivative of SISOMYCIN, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity.
1 2D Structure

Netilmicin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;sulfuric acid
2.1.2 InChI
InChI=1S/C21H41N5O7.H2O4S/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20;1-5(2,3)4/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3;(H2,1,2,3,4)/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+;/m1./s1
2.1.3 InChI Key
PQHZSWZPVGHDEZ-UIQTUGNFSA-N
2.1.4 Canonical SMILES
CCNC1CC(C(C(C1OC2C(C(C(CO2)(C)O)NC)O)O)OC3C(CC=C(O3)CN)N)N.OS(=O)(=O)O
2.1.5 Isomeric SMILES
CCN[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]2[C@@H]([C@H]([C@@](CO2)(C)O)NC)O)O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N.OS(=O)(=O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Certomycin

2. Ntromicine

3. Netillin

4. Netilmicin

5. Netilmicin Sulfate

6. Netrocin

7. Netromicina

8. Netromycin

9. Netromycine

10. Sch 20569

11. Sch-20569

12. Sch20569

2.2.2 Depositor-Supplied Synonyms

1. Netilmicin Sulfate

2. 56391-57-2

3. (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4-amino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Sulfate

4. Akos015961218

5. Ac-22349

2.3 Create Date
2007-12-08
3 Chemical and Physical Properties
Molecular Weight 573.7 g/mol
Molecular Formula C21H43N5O11S
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count16
Rotatable Bond Count8
Exact Mass573.26797838 g/mol
Monoisotopic Mass573.26797838 g/mol
Topological Polar Surface Area283 Ų
Heavy Atom Count38
Formal Charge0
Complexity754
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)


API Reference Price

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20-Apr-2021
28-Jun-2023
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