(2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol; sulfuric acid

• ChemBase ID: 155167
• Molecular Formular: C23H47N5O18S
• Molecular Mass: 713.70698
• Monoisotopic Mass: 713.26368069
• 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.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.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
• InChI: InChI=1S/C23H45N5O14.H2O4S/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;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1
• InChIKey: LJRDOKAZOAKLDU-UDXJMMFXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol; sulfuric acid; (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; sulfuric acid
• IUPAC Traditional name: (2R,3S,4R,5R,6S)-5-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol; sulfuric acid; paromomycin; sulfuric acid
• Synonyms: Paromomycin sulfate salt; Paromomycin sulfate; Paromomycin sulfate salt 硫酸盐

Database IDs

• CAS Number: 1263-89-4
• EC Number: 215-031-7
• MDL Number: MFCD00079278
• Beilstein Number: 5715182
• PubChem SID: 162249305; 24898967; 24898585; 24278662
• PubChem CID: 441375

CALCULATED PROPERTIES

• Acid pKa: 12.227455
• H Acceptors: 19
• H Donor: 13
• LogD (pH = 5.5): -21.56059
• LogD (pH = 7.4): -14.423654
• Log P: -8.308296
• Molar Refractivity: 134.2428 cm^3
• Polarizability: 57.386707 Å^3
• Polar Surface Area: 347.32 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL (store stock solution at 2-8°C. Stable at 37°C for 5 days.); H2O: soluble50 mg/mL, slightly turbid, colorless
• Apperance: powder

Safety Information

• RTECS: WK2320000
• German water hazard class: 2

Product Information

• Purity: >98.0% (TLC); ≥98%; ≥98% (TLC); 95+%
• Potency: ≥675 μg per mg
• Suitability: plant cell culture tested; suitable for cell culture
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C23H45N5O14 · H2SO4

DETAILS

Sigma Aldrich - P9297

Application
Paromomycin is a broad spectrum aminoglycoside antibiotic produced by Streptomyces rimosus var. paromomycinus. It has in vitro and in vivo activity similar to neomycin. It is effective against Gram-negative bacteria, Gram-positive bacteria, some protozoan species, and limited antihelminth. It is used to study bacterial protein synthesis at the level of 16S ribosomal RNA and 30S ribosome assembly. Paromomycin is used to study cytosine-cytosine (CC) mismatch-containing RNA molecules1 and is used to inhibit Cryptosporidium infection of a human enterocyte cell line2.
Biochem/physiol Actions
Paromomycin inhibits the initiation and elongation steps of protein synthesis by binding to 16S ribosomal RNA. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced and leads to cell death.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - P5057

Application
Recommended for use in cell culture applications at 100 mg/L.
Biochem/physiol Actions
Paromomycin inhibits the initiation and elongation steps of protein synthesis by binding to 16S ribosomal RNA. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced and leads to cell death.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - P8692

Application
Paromomycin, monomycin, is an aminoglycoside antibiotic used to select genetically transformed plants and plant cells.
Biochem/physiol Actions
Paromomycin inhibits the initiation and elongation steps of protein synthesis by binding to 16S ribosomal RNA. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced and leads to cell death.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 76261

Biochem/physiol Actions
Paromomycin inhibits the initiation and elongation steps of protein synthesis by binding to 16S ribosomal RNA. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced and leads to cell death.