Apramycin (CED0004492)

Record Information

Version

1.0

Creation Date

2016-05-22 05:09:57 UTC

Update Date

2026-05-14 18:09:27 UTC

Accession Number

CHEM018337

Identification

Common Name

Apramycin

Class

Small Molecule

Description

Apramycin is an organic compound with the chemical formula C21H41N5O11. Apramycin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 539.58 g/mol, Apramycin is a heavy molecule. This compound is associated with five recorded sources, including drinking water and water supply, specifically drinking water. It is also found in healthcare, pharmaceuticals and veterinary products as antibiotics, as well as in building and construction materials such as tents or canopies. Additionally, it is released from electrical and electronic equipment, including amplifiers and antennas. Recorded exposure routes for Apramycin include oral and inhalation.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine	ChEBI
4-O-(3alpha-Amino-6alpha-((4-amino-4-deoxy-alpha-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8beta-hydroxy-7beta-(methylamino)pyrano(3,2-b)pyran-2alpha-yl)-2-deoxy-D-streptamine	ChEBI
Apramicina	ChEBI
Apramycine	ChEBI
Apramycinum	ChEBI
Nebramycin factor 2	ChEBI
Nebramycin II	ChEBI
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-a-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-a-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine	Generator
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine	Generator
4-O-(3a-Amino-6a-((4-amino-4-deoxy-a-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8b-hydroxy-7b-(methylamino)pyrano(3,2-b)pyran-2a-yl)-2-deoxy-D-streptamine	Generator
4-O-(3Α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamine	Generator
Apramycin sulfate	MeSH

Chemical Formula

C₂₁H₄₁N₅O₁₁

Average Molecular Mass

539.577 g/mol

Monoisotopic Mass

539.280 g/mol

CAS Registry Number

37321-09-8

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)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol

Traditional Name

apramycin

SMILES

CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H41N5O11/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/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1

InChI Key

XZNUGFQTQHRASN-XQENGBIVSA-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
Hexose monosaccharide
Aminocyclitol or derivatives
Cyclohexylamine
Cyclohexanol
Oxane
Cyclitol or derivatives
Monosaccharide
1,3-aminoalcohol
Cyclic alcohol
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Secondary amine
Acetal
Secondary aliphatic amine
Organopnictogen compound
Primary aliphatic amine
Organonitrogen compound
Primary alcohol
Organic nitrogen compound
Amine
Alcohol
Primary amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:2790 )
aminoglycoside (CHEBI:2790 )
2-deoxystreptamine derivative (CHEBI:2790 )

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	53.3 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-6.5	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	9.73	ChemAxon
Physiological Charge	5	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	283.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.91 m³·mol⁻¹	ChemAxon
Polarizability	54.29 Å³	ChemAxon
Number of Rings	4	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 LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03mi-0609060000-be32be8bb819fe00bb8f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0903010000-245a139b0e513ad0f210	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03ka-6925000000-5e9c617ea15eb45bbc05	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0729-2973240000-f9d27a3b85b6fc213321	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fu-1913010000-0b9c2b857514700bb081	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-114i-7920000000-fa96e884539e16c3ec58	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
7016.0	Log mg/kg	[3900:12000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
115	Drinking water	Drinking water & water supply	Not Available
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
503	Tents Or Canopies	Building & Construction	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
596	Acaricides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
696	Nanotechnology	Industrial manufacturing & chemical processing	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Gap junction beta-2 protein	P29033	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Human immunodeficiency virus type 1 REV	Q77Y21	Human immunodeficiency virus 1	Predicted (SEA)	0.389246
Click to view 3D structure	CD44 antigen	P16070	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	CD44 antigen	P15379	Mus musculus	Predicted (SEA)	1.32344
Click to view 3D structure	Gap junction alpha-1 protein	P17302	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Beta-ketoacyl-[acyl-carrier-protein] synthase III	P0A6R0	Escherichia coli (strain K12)	Predicted (SEA)	0.467095
Click to view 3D structure	Alpha-amylase	Q7M328	Sus scrofa domesticus	Predicted (SEA)	0.934191
Click to view 3D structure	N-acetyllactosaminide alpha-1,3-galactosyltransferase	P50127	Sus scrofa	Predicted (SEA)	6.92858
Click to view 3D structure	Endo-beta-N-acetylglucosaminidase	Q9ZB22	Arthrobacter protophormiae	Predicted (SEA)	4.43741
Click to view 3D structure	Aminoglycoside acetyltransferase	Q70E71	Enterococcus durans	Predicted (SEA)	11.9109
Click to view 3D structure	Killer cell lectin-like receptor subfamily B member 1A	P27471	Rattus norvegicus	Predicted (SEA)	4.5931
Click to view 3D structure	3-oxoacyl-[acyl-carrier-protein] synthase 3	C3TDZ2	Escherichia coli	Predicted (SEA)	0.856341
Click to view 3D structure	Heparanase	Q9Y251	Humans	Predicted (SEA)	3.73676
Click to view 3D structure	Peptidoglycan-N-acetylglucosamine deacetylase	Q8DP63	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Predicted (SEA)	19.3845
Click to view 3D structure	Galectin-3	P17931	Humans	Predicted (SEA)	29.972
Click to view 3D structure	Lectin	B4EH87	Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))	Predicted (SEA)	17.1268
Click to view 3D structure	E-selectin	P98105	Rattus norvegicus	Predicted (SEA)	3.89246
Click to view 3D structure	Type 1 fimbrin D-mannose specific adhesin	P08191	Escherichia coli K-12	Predicted (SEA)	20.1629
Click to view 3D structure	Interferon gamma	P01579	Humans	Predicted (SEA)	2.25763
Click to view 3D structure	Sucrase-isomaltase, intestinal	P23739	Rattus norvegicus	Predicted (SEA)	15.0249
Click to view 3D structure	Neurotrophic factor BDNF precursor form	P23560	Humans	Predicted (SEA)	3.42537
Click to view 3D structure	Pleiotrophin	P21246	Humans	Predicted (SEA)	3.42537
Click to view 3D structure	Sialic acid-binding Ig-like lectin 7	Q9Y286	Humans	Predicted (SEA)	3.50322
Click to view 3D structure	Bone morphogenetic protein 6	P22004	Humans	Predicted (SEA)	3.89246
Click to view 3D structure	Platelet factor 4	P02776	Humans	Predicted (SEA)	3.89246