(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 31282-04-9
• EC Number: 250-545-5
• MDL Number: MFCD06795479
• Beilstein Number: 6755837
• PubChem SID: 24895568; 162227295; 24895698; 24895807; 24895410
• PubChem CID: 23777801

CALCULATED PROPERTIES

• 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 cm^3
• Polarizability: 48.133503 Å^3
• Polar Surface Area: 272.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• 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.)
• Apperance: lyophilized powder; powder

Safety Information

• RTECS: WK2130000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2810; 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-41-42/43
• Safety Statements: 22-26-28-36/37/39-45; 23-26-28-36/37/39-45
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300 +H310 + H330-H318-H334; H301 + H311-H318-H330-H334
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P280-P284-P301 + P310-P305 + P351 + P338-P310
• 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; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 1; UN 3462 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ~65% (HPLC); ≥60% (HPAE); ≥90% (HPLC)
• Concentration: ~100 mg/mL in H2O; 45-60 mg/mL in H2O
• Suitability: plant cell culture tested; suitable for cell culture; suitable for insect cell culture
• Sterility: 0.22 μm filtered; γ-irradiated
• Purified By: ion-exchange chromatography
• Empirical Formula (Hill Notation): C20H37N3O13

DETAILS

Sigma Aldrich - H0654

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

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

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

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 - 56685

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

Sigma Aldrich - H9773

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

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.