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31282-04-9 molecular structure
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(2S,3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-{[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-[(1R)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)-tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol

ChemBase ID: 133018
Molecular Formular: C20H37N3O13
Molecular Mass: 527.52008
Monoisotopic Mass: 527.23263826
SMILES and InChIs

SMILES:
CN[C@H]1C[C@H]([C@@H]([C@H]([C@@H]1O)O[C@H]1[C@@H]2[C@H]([C@H]([C@H](O1)CO)O)O[C@]1(O2)[C@@H]([C@H]([C@H]([C@H](O1)[C@@H](CO)N)O)O)O)O)N
Canonical SMILES:
OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](N)C[C@@H]([C@H]2O)NC)[C@@H]2[C@H]([C@H]1O)O[C@@]1(O2)O[C@H]([C@@H](CO)N)[C@@H]([C@@H]([C@H]1O)O)O
InChI:
InChI=1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6-,7+,8-,9+,10-,11+,12-,13+,14-,15-,16+,17+,18-,19+,20+/m1/s1
InChIKey:
GRRNUXAQVGOGFE-XKIAHZFYSA-N

Cite this record

CBID:133018 http://www.chembase.cn/molecule-133018.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-{[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-[(1R)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)-tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
IUPAC Traditional name
(2S,3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-{[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-[(1R)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)-tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
Synonyms
Hygromycin B from Streptomyces hygroscopicus
Hygromycin B solution from Streptomyces hygroscopicus
潮霉素 B 来源于吸水链霉菌
潮霉素 B 溶液 来源于吸水链霉菌
CAS Number
31282-04-9
EC Number
250-545-5
MDL Number
MFCD06795479
Beilstein Number
6755837
PubChem SID
24895568
24895807
162227295
24895698
24895410
PubChem CID
23777801

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.410827  H Acceptors 16 
H Donor 11  LogD (pH = 5.5) -14.653606 
LogD (pH = 7.4) -10.57404  Log P -6.549424 
Molar Refractivity 114.0538 cm3 Polarizability 48.133503 Å3
Polar Surface Area 272.06 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL (As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 30 days.) expand Show data source
Apperance
lyophilized powder expand Show data source
powder expand Show data source
RTECS
WK2130000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2810 expand Show data source
3462 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
Risk Statements
26/27/28-41-42/43 expand Show data source
Safety Statements
22-26-28-36/37/39-45 expand Show data source
23-26-28-36/37/39-45 expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300 +H310 + H330-H318-H334 expand Show data source
H301 + H311-H318-H330-H334 expand Show data source
GHS Precautionary statements
P260-P264-P280-P284-P301 + P310-P302 + P350 expand Show data source
P260-P280-P284-P301 + P310-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, 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
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2810 6.1/PG 1 expand Show data source
UN 3462 6.1/PG 1 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
~65% (HPLC) expand Show data source
≥60% (HPAE) expand Show data source
≥90% (HPLC) expand Show data source
Concentration
~100 mg/mL in H2O expand Show data source
45-60 mg/mL in H2O expand Show data source
Suitability
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for insect cell culture expand Show data source
Sterility
0.22 μm filtered expand Show data source
γ-irradiated expand Show data source
Purified By
ion-exchange chromatography expand Show data source
Empirical Formula (Hill Notation)
C20H37N3O13 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - H0654 external link
Application
在许多细胞培养应用中,潮霉素已用于在转移潮霉素磷酸转移酶基因后选择耐药稳定的转染子。
Hygromycin B is an aminoglycoside antibiotic produced by the bacterium Streptomyces hygroscopicus that kills bacteria, fungi and higher eukaryotic cells by inhibiting protein synthesis. It is used for the selection and maintenance of prokaryotic and eukaryotic cells that contain the hygromycin resistance gene. It is used in gene transfer experiments as a selection agent. Product H0654 is a solution that comes ≥60% (HPAE) and 45-60 mg/mL in H2O.
Biochem/physiol Actions
抗菌剂和抗真菌剂。作用方式:在原核生物和真核生物中,通过诱导 mRNA 模板的误读而抑制蛋白质合成。它可选择性透入因病毒感染而变得可渗透的细胞。
Sigma Aldrich - H5527 external link
Application
在许多细胞培养应用中,潮霉素已用于在转移潮霉素磷酸转移酶基因后选择耐药稳定的转染子。
Hygromycin B is an aminoglycoside antibiotic produced by the bacterium Streptomyces hygroscopicus that kills bacteria, fungi and higher eukaryotic cells by inhibiting protein synthesis. It is used for the selection and maintenance of prokaryotic and eukaryotic cells that contain the hygromycin resistance gene. It is used in gene transfer experiments as a selection agent. Product H5527 is a solution that is ≥60% (HPAE), 45-60 mg/mL in H2O, and γ-irradiated .
Biochem/physiol Actions
抗菌剂和抗真菌剂。作用方式:在原核生物和真核生物中,通过诱导 mRNA 模板的误读而抑制蛋白质合成。它可选择性透入因病毒感染而变得可渗透的细胞。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - H3274 external link
Biochem/physiol Actions
Mode of Action: Blocks polypeptide synthesis and inhibits elongation. For use in the selection and maintenance of prokaryotic and eukaryotic cells.
Preparation Note
通过离子交换色谱纯化
Application
Use to study protein synthesis at the level of 70S ribosome translocation and mRNA template misreading. Use as a selection agent for hygromycin resistance gene transformed cells. Recommended for use as a selection agent at 100-800 μg/mL.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - H7772 external link
Biochem/physiol Actions
Mode of Action: Blocks polypeptide synthesis and inhibits elongation. For use in the selection and maintenance of prokaryotic and eukaryotic cells.
Application
Hygromycin B is an aminoglycoside antibiotic produced by the bacterium Streptomyces hygroscopicus that kills bacteria, fungi and higher eukaryotic cells by inhibiting protein synthesis. It is used for the selection and maintenance of prokaryotic and eukaryotic cells that contain the hygromycin resistance gene. It is used in gene transfer experiments as a selection agent1,2,3.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - H9773 external link
Biochem/physiol Actions
Mode of Action: Blocks polypeptide synthesis and inhibits elongation. For use in the selection and maintenance of prokaryotic and eukaryotic cells.
Application
Hygromycin B is used in molecular biology as a selection agent for plant cells transformed with selectable marker genes such as hygromycin phosphotransferase (hpt).
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 56682 external link
Application
Hygromycin has been used to select drug-resistant stable transfectants after transfer of the hygromycin phosphotransferase gene in a variety of cell culture applications.
Biochem/physiol Actions
Antibacterial and antifungal. Mode of action: Inhibition of protein synthesis, by inducing the misreading of the m-RNA template in prokaryotes and eukaryotes. It selectively penetrates cells that have been rendered permeable by virus infection.
Sigma Aldrich - 56685 external link
Biochem/physiol Actions
Mode of Action: Blocks polypeptide synthesis and inhibits elongation. For use in the selection and maintenance of prokaryotic and eukaryotic cells.
Other Notes
Specifically inhibits protein synthesis at translocation1; Purification of hygromycin B phosphotransferase by affinity column chromatography2

REFERENCES

REFERENCES

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PATENTS

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