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Netilmicin

Netilmicin

Synopsis, 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

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 Formula	C₂₁H₄₃N₅O₁₁S
Molecular Weight	573.7 g/mol
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	8
Exact Mass	573.26797838 g/mol
Monoisotopic Mass	573.26797838 g/mol
Topological Polar Surface Area	283 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	754
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)