paromomycin   Click here for help

GtoPdb Ligand ID: 12160

Synonyms: aminosidine | catenulin | Humatin® | monomycin A
Approved drug PDB Ligand
paromomycin is an approved drug (FDA (1969))
Compound class: Natural product or derivative
Comment: Paromomycin belongs to the aminoglycoside class of antibacterial compounds and was originally isolated from Streptomyces krestomuceticus. It is used as an antiprotozoal drug and is included in the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below).
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 19
Hydrogen bond donors 13
Rotatable bonds 9
Topological polar surface area 347.32
Molecular weight 615.3
XLogP -6.85
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O[C@H]1O[C@@H](CN)[C@H]([C@@H]([C@H]1N)O)O)O)O[C@@H]1[C@@H](O)[C@H](N)C[C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1N)O)O)N
Isomeric SMILES C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)N)O[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)CN)O)O)N)O)O)N
InChI InChI=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 Key UOZODPSAJZTQNH-LSWIJEOBSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1969))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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]oxyoxane-3,4-diol
International Nonproprietary Names Click here for help
INN number INN
939 paromomycin
Synonyms Click here for help
aminosidine | catenulin | Humatin® | monomycin A
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Paromomycin, monomycin, hydroxymycin
Other databases
CAS Registry No. 7542-37-2 (source: Scifinder)
ChEBI CHEBI:7934
ChEMBL Ligand CHEMBL370143
DrugBank Ligand DB01421
DrugCentral Ligand 2067
GtoPdb PubChem SID 472319282
PubChem CID 165580
RCSB PDB Ligand PAR
Search Google for chemical match using the InChIKey UOZODPSAJZTQNH-LSWIJEOBSA-N
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UniChem Compound Search for chemical match using the InChIKey UOZODPSAJZTQNH-LSWIJEOBSA-N
UniChem Connectivity Search for chemical match using the InChIKey UOZODPSAJZTQNH-LSWIJEOBSA-N
Wikipedia Paromomycin