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1263-89-4 molecular structure
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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

ChemBase ID: 1229
Molecular Formular: C23H45N5O14
Molecular Mass: 615.6285
Monoisotopic Mass: 615.29630115
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

Cite this record

CBID:1229 http://www.chembase.cn/molecule-1229.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
1263-89-4
PubChem SID
46505391
160964689
PubChem CID
165580

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 57.386707 Å3
Polar Surface Area 347.32 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -2.92  LOG S -0.89 
Solubility (Water) 7.97e+01 g/l 

PROPERTIES

PROPERTIES

Product Information Bioassay(PubChem)
Classification
Rare Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01421 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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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PATENTS

PATENTS

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INTERNET

INTERNET

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