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53179-09-2 molecular structure
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bis((2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol); pentakis(sulfuric acid)

ChemBase ID: 155340
Molecular Formular: C38H84N10O34S5
Molecular Mass: 1385.44516
Monoisotopic Mass: 1384.37549482
SMILES and InChIs

SMILES:
C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H](CC=C(O1)CN)N)N)N)O.C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H](CC=C(O1)CN)N)N)N)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
Canonical SMILES:
OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N.NCC1=CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OC[C@]([C@@H]([C@H]1O)NC)(C)O)N)N
InChI:
InChI=1S/2C19H37N5O7.5H2O4S/c2*1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;5*1-5(2,3)4/h2*3,9-18,24-27H,4-7,20-23H2,1-2H3;5*(H2,1,2,3,4)/t2*9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+;;;;;/m11...../s1
InChIKey:
CIKNYWFPGZCHDL-ZHFUJENKSA-N

Cite this record

CBID:155340 http://www.chembase.cn/molecule-155340.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
bis((2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol); pentakis(sulfuric acid)
IUPAC Traditional name
bis(SISO); pentakis(sulfuric acid)
Synonyms
Sisomicin sulfate salt
CAS Number
53179-09-2
EC Number
258-414-4
PubChem SID
162249478
PubChem CID
439243

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
S7796 external link Add to cart Please log in.
Data Source Data ID
PubChem 439243 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.548462  H Acceptors 12 
H Donor LogD (pH = 5.5) -18.497313 
LogD (pH = 7.4) -11.9235935  Log P -4.3185678 
Molar Refractivity 110.3207 cm3 Polarizability 45.65683 Å3
Polar Surface Area 213.72 Å2 Rotatable Bonds 12 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
RTECS
WK2288000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
61-20/21/22 expand Show data source
Safety Statements
53-22-36/37/39-45 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H312-H332-H360 expand Show data source
GHS Precautionary statements
P201-P280-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥80% (TLC) expand Show data source
Linear Formula
2C19H37N5O7 · 5H2SO4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - S7796 external link
Application
Sisomicin is an aminoglycoside antibiotic isolated from Micromonopora inyoensis. It is effective against most strains of Klebsiellk spp., Escherichia coli, P. aeruginosa, Enterobacter and Proteus spp.. It is a potential treatment for conjunctiva 1. It is used in disk and tube dilution sensitivity test2.
Biochem/physiol Actions
Sisomicin interferes with protein synthesis at the level of functional ribosome assembly. The mechanism is similar to that of gentamycin. Sisomicin closely resembles gentamicin but is more effective against Pseudomonas aeruginosa and indole-positive Proteus3.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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