paromomycin (CED0003718)

Record Information
Version1.0
Creation Date2016-06-03 10:17:55 UTC
Update Date2026-05-14 17:00:17 UTC
Accession NumberCHEM042830
Identification
Common Nameparomomycin
ClassSmall Molecule
Description
Paromomycin is a compound with the chemical formula C23H45N5O14. Paromomycin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 615.63 g/mol, paromomycin is a heavy molecule. This compound is found in or released from seven recorded sources. These include pharmaceuticals and veterinary products, specifically antibiotics and intestinal antiinfectives, as well as electrical and electronic equipment such as video games and television systems. It is also associated with food, food processing and cookware, including processing meats and agglomerated sugar products, and household cleaning and consumer products, specifically non electric simulated smoking devices. Recorded exposure routes for paromomycin include oral and inhalation. At the molecular level, paromomycin interacts with three recorded protein targets. It acts as an inhibitor of the small ribosomal subunit protein uS2 (RPSA), the small ribosomal subunit protein uS10 (rpsJ), and the ribosomal protein uL16-like (RPL10L).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranosideChEBI
AminosidinChEBI
AminosidineChEBI
CatenulinChEBI
CrestomycinChEBI
EstomycinChEBI
HydroxymycinChEBI
Monomycin aChEBI
Neomycin eChEBI
ParomomicinaChEBI
Paromomycin IChEBI
ParomomycineChEBI
ParomomycinumChEBI
PaucimycinChEBI
PaucimycinumChEBI
R 400ChEBI
R-400ChEBI
Zygomycin a1ChEBI
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-b-L-idopyranosyl)-b-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-a-D-glucopyranosideGenerator
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-β-L-idopyranosyl)-β-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-α-D-glucopyranosideGenerator
PRMHMDB
Paramomycin sulfateHMDB
Paramomycin sulphateHMDB
GabbromycinHMDB
Parke davis brand OF paromomycin sulfateHMDB
Paromomycin, beta-D-glucopyranosyl-isomerHMDB
Sulfate, paromomycinHMDB
HumatinHMDB
Phosphate, paromomycinHMDB
Cheminova brand OF paromomycin sulfateHMDB
Paromomycin sulfate (1:1)HMDB
Pfizer brand OF paromomycin sulfateHMDB
beta-D-Glucopyranosyl-isomer paromomycinHMDB
Monarch brand OF paromomycin sulfateHMDB
ParamomycinHMDB
Paromomycin phosphateHMDB
Paromomycin sulfateHMDB
Paromomycin sulfate (2:5)HMDB
Paromomycin, beta D glucopyranosyl isomerHMDB
Chemical FormulaC23H45N5O14
Average Molecular Mass615.629 g/mol
Monoisotopic Mass615.296 g/mol
CAS Registry Number7542-37-2
IUPAC Name(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol
Traditional Nameparomomycin
SMILESNC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
InChI KeyUOZODPSAJZTQNH-LSWIJEOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent4,5-disubstituted 2-deoxystreptamines
Alternative Parents
Substituents
  • 4,5-disubstituted 2-deoxystreptamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Aminocyclitol or derivatives
  • Cyclohexanol
  • Cyclohexylamine
  • Cyclitol or derivatives
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility79.7 g/LALOGPS
logP-2.9ALOGPS
logP-8.3ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)12.23ChemAxon
pKa (Strongest Basic)9.94ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area347.32 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity134.24 m³·mol⁻¹ChemAxon
Polarizability60.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
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Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
11600.0Log mg/kg[6500:21000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
254Intestinal antiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureHuman immunodeficiency virus type 1 REVQ77Y21Human immunodeficiency virus 1Predicted (SEA)0.0778492
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)0.389246
Beta-ketoacyl-[acyl-carrier-protein] synthase III structureClick to view 3D structureBeta-ketoacyl-[acyl-carrier-protein] synthase IIIP0A6R0Escherichia coli (strain K12)Predicted (SEA)0.0778492
Gap junction alpha-1 protein structureClick to view 3D structureGap junction alpha-1 proteinP17302HumansPredicted (SEA)0.389246
Click to view 3D structure3-oxoacyl-[acyl-carrier-protein] synthase 3C3TDZ2Escherichia coliPredicted (SEA)0.311397
Click to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)0.622794
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)2.64687
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)1.71268
Click to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)1.71268
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)5.3716
Click to view 3D structureAlpha-amylaseQ7M328Sus scrofa domesticusPredicted (SEA)1.08989
Click to view 3D structureType 1 fimbrin D-mannose specific adhesinP08191Escherichia coli K-12Predicted (SEA)7.00643
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)194.934
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)12.2223
Click to view 3D structureKiller cell lectin-like receptor subfamily B member 1AP27471Rattus norvegicusPredicted (SEA)2.02408
Lethal factor structureClick to view 3D structureLethal factorP15917Bacillus anthracisPredicted (SEA)37.1341
Heparanase structureClick to view 3D structureHeparanaseQ9Y251HumansPredicted (SEA)2.17978
Click to view 3D structureAminoglycoside acetyltransferaseQ70E71Enterococcus duransPredicted (SEA)14.9471
Sialic acid-binding Ig-like lectin 7 structureClick to view 3D structureSialic acid-binding Ig-like lectin 7Q9Y286HumansPredicted (SEA)1.79053
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)3.89246
Click to view 3D structureSucrase-isomaltase, intestinalP23739Rattus norvegicusPredicted (SEA)10.821
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)2731.34
Click to view 3D structureCytidine deaminaseP56389Mus musculusPredicted (SEA)36.122
Click to view 3D structureRibonuclease pancreaticP61823Bos taurusPredicted (SEA)28.1814
Click to view 3D structurePA-I galactophilic lectinQ05097Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)9.41976
Concentrations
Not Available
External Links
DrugBank IDDB01421
HMDB IDHMDB0015490
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00018808
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPAR
Wikipedia LinkParomomycin
Chemspider ID145115
ChEBI ID7934
PubChem Compound ID165580
Kegg Compound IDC00832
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18447603
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18947845
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8036682
4. Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58.