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(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
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ChemBase ID:
1229
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Molecular Formular:
C23H45N5O14
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Molecular Mass:
615.6285
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Monoisotopic Mass:
615.29630115
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SMILES and InChIs
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
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Cite this record
CBID:1229 http://www.chembase.cn/molecule-1229.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(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
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IUPAC Traditional name
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(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
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Brand Name
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Synonyms
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Aminosidin
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Aminosidine
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Paramomycin sulfate
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paromomycin
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Paromomycin
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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12.227455
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H Acceptors
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19
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H Donor
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13
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LogD (pH = 5.5)
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-21.56059
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LogD (pH = 7.4)
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-14.423654
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Log P
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-8.308296
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Molar Refractivity
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134.2428 cm3
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Polarizability
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57.386707 Å3
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Polar Surface Area
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347.32 Å2
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Rotatable Bonds
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9
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Lipinski's Rule of Five
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false
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Log P
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-2.92
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LOG S
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-0.89
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Solubility (Water)
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7.97e+01 g/l
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PROPERTIES
PROPERTIES
Product Information
Bioassay(PubChem)
Classification
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Rare Genuine Natural Compounds
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Show
data source
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DETAILS
DETAILS
DrugBank
DrugBank -
DB01421
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Item |
Information |
Drug Groups
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approved; investigational |
Description
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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 |
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Enteric bacteria and other eubacteria |
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Absorption |
Poorly absorbed after oral administration, with almost 100% of the drug recoverable in the stool. |
References |
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Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58.
[Pubmed]
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External Links |
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PATENTS
PATENTS
PubChem Patent
Google Patent