Netilmicin (CED0004471)

Record Information

Version

1.0

Creation Date

2016-05-25 18:23:53 UTC

Update Date

2026-05-14 16:54:02 UTC

Accession Number

CHEM022208

Identification

Common Name

Netilmicin

Class

Small Molecule

Description

Netilmicin is an organic compound with the chemical formula C21H41N5O7 and an average molecular weight of 475.58 g/mol. Netilmicin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. This compound is identified as an inhibitor of the small ribosomal subunit protein uS12 (rpsL). It is found in or released from five recorded sources, including indoor air, antennas within electrical and electronic equipment, and various healthcare, pharmaceuticals, and veterinary products such as antibiotics, antiinfectives, and aminoglycoside antibacterials. Recorded exposure routes for the substance include oral, intravenous, intramuscular, ophthalmic, and inhalation pathways.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-N-Ethylsisomicin	ChEBI
O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine	ChEBI
O-3-Deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine	Generator
O-3-Deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(1)-ethyl-D-streptamine	Generator
Netilmycin	HMDB

Chemical Formula

C₂₁H₄₁N₅O₇

Average Molecular Mass

475.580 g/mol

Monoisotopic Mass

475.301 g/mol

CAS Registry Number

56391-56-1

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}-3-methyl-4-(methylamino)oxane-3,5-diol

Traditional Name

netilmicin sulfate

SMILES

CCN[C@@H]1C[C@H](N)[C@@H](O[C@H]2OC(CN)=CC[C@H]2N)[C@H](O)[C@H]1O[C@H]1OC[C@H](O)[C@@H](NC)[C@@]1(C)O

InChI Identifier

InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)15(28)17(13)33-20-21(2,29)18(25-3)14(27)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15+,16-,17+,18-,19-,20-,21-/m1/s1

InChI Key

ZBGPYVZLYBDXKO-HILBYHGXSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminocyclitol glycosides

Alternative Parents

Substituents

Amino cyclitol glycoside
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Secondary alcohol
Acetal
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Oxacycle
Primary aliphatic amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Alcohol
Primary amine
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:7528 )
aminoglycoside antibiotic (CHEBI:7528 )
amino cyclitol glycoside (CHEBI:7528 )
beta-L-arabinoside (CHEBI:7528 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	8.43 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-3.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.49	ChemAxon
pKa (Strongest Basic)	9.97	ChemAxon
Physiological Charge	5	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	119.84 m³·mol⁻¹	ChemAxon
Polarizability	50.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4l-9130200000-0f999ffbda4a03dfd7be	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00fu-9521302000-5b2fbb5b6d2df6d28c2d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05rr-1114900000-704797287b90a8a5d0c0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1719200000-508e95c04a47ba147837	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dr-6901000000-1ff8e064a2101055e2f9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-2900100000-3bc695e8d76ea5bf8985	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0007-9203300000-4f27c77ab5ce05c6f2b2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f7o-6942000000-646ea1cd47c80a2852ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900500000-45a63b16efc5d3ae16da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-1902300000-d078ac1d0a2f0b43602a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9600000000-32d974c667070b20c8fd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0412900000-1c09ce07c595899ea8f6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0605900000-760bbc585615d1f4b174	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-007a-6932300000-490225267dadfd2ffa65	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
6450.0	Log mg/kg	[3600:11000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
344	Aminoglycoside antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
395	Antiinfectives	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
631	Anthraquinone Dyes	Textiles, leather & furnishings	Not Available
633	Azo Dyes	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Netilmicin Action Pathway

Netilmicin Drug Metabolism Action Pathway

Netilmicin Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Gap junction beta-2 protein	P29033	Humans	Predicted (SEA)	1.63483
Click to view 3D structure	Gap junction alpha-1 protein	P17302	Humans	Predicted (SEA)	1.94623
Click to view 3D structure	Human immunodeficiency virus type 1 REV	Q77Y21	Human immunodeficiency virus 1	Predicted (SEA)	1.24559
Click to view 3D structure	Beta-ketoacyl-[acyl-carrier-protein] synthase III	P0A6R0	Escherichia coli (strain K12)	Predicted (SEA)	2.95827
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	7183.46
Click to view 3D structure	3-oxoacyl-[acyl-carrier-protein] synthase 3	C3TDZ2	Escherichia coli	Predicted (SEA)	4.82665
Click to view 3D structure	DNA topoisomerase 2-alpha	P11388	Humans	Predicted (SEA)	2323.49
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	7742.42
Click to view 3D structure	Beta-chimaerin	P52757	Humans	Predicted (SEA)	300.187
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	7727.78
Click to view 3D structure	Transient receptor potential cation channel subfamily V member 1	Q8NER1	Humans	Predicted (SEA)	6756.77
Click to view 3D structure	Maltase-glucoamylase	O43451	Humans	Predicted (SEA)	559.892
Click to view 3D structure	Sucrase-isomaltase, intestinal	P14410	Humans	Predicted (SEA)	105.953
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	7458.34
Click to view 3D structure	DIS3-like exonuclease 2	Q8IYB7	Humans	Predicted (SEA)	20.0851
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	7572.32
Click to view 3D structure	Adenosine receptor A1	P28190	Bos taurus	Predicted (SEA)	5190.91
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	7536.12
Click to view 3D structure	Neuraminidase	A5Z252	Influenza A virus	Predicted (SEA)	1880.45
Click to view 3D structure	Neuraminidase	P03468	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	Predicted (SEA)	2775.4
Click to view 3D structure	Neuraminidase	Q07599	Influenza A virus (strain A/Duck/Ukraine/1/1963 H3N8)	Predicted (SEA)	1237.18
Click to view 3D structure	Motilin receptor	A5A4K8	Oryctolagus cuniculus	Predicted (SEA)	7.08428
Click to view 3D structure	Aminoglycoside acetyltransferase	Q70E71	Enterococcus durans	Predicted (SEA)	80.029
Click to view 3D structure	Solute carrier organic anion transporter family member 1B1	Q9Y6L6	Humans	Predicted (SEA)	6256.12
Click to view 3D structure	Chitin synthase 1	P08004	Saccharomyces cerevisiae S288c	Predicted (SEA)	38.1461