(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

• ChemBase ID: 1229
• Molecular Formular: C23H45N5O14
• Molecular Mass: 615.6285
• Monoisotopic Mass: 615.29630115
• SMILES: O([C@H]1[C@H](O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2N)CO)[C@@H](N)C[C@@H](N)[C@@H]1O)[C@@H]1O[C@@H]([C@@H](O[C@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2N)CN)[C@H]1O)CO
• 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
• 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
• InChIKey: UOZODPSAJZTQNH-LSWIJEOBSA-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
• 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
• Brand Name: Humatin
• Synonyms: Aminosidin; Aminosidine; Paramomycin sulfate; paromomycin; Paromomycin

Database IDs

• CAS Number: 1263-89-4
• PubChem SID: 160964689; 46505391
• PubChem CID: 165580

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.92
• LOG S: -0.89
• Solubility (Water): 7.97e+01 g/l

PROPERTIES

Product Information

• Classification: Rare Genuine Natural Compounds

DETAILS

DrugBank - DB01421

• Drug Groups: approved; investigational
• Description: An oligosaccharide antibiotic produced by various streptomyces. [PubChem]
• Indication: For the treatment of acute and chronic intestinal amebiasis (it is not effective in extraintestinal amebiasis). Also for the management of hepatic coma as adjunctive therapy.
• Pharmacology: Paromomycin is a broad spectrum aminoglycoside antibiotic produced by Streptomyces rimosus var. paromomycinus. The in vitro and in vivo antibacterial action of paromomycin closely parallels that of neomycin.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Poorly absorbed after oral administration, with almost 100% of the drug recoverable in the stool.
• References: Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58. Pubmed