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Hygromycin B structure
Hygromycin B structure

Hygromycin B

Iupac Name:(3'R,3aS,4S,4'R,5'R,6R,6'R,7S,7aS)-4-[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-[(1S)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
CAS No.: 31282-04-9
Molecular Weight:527.524
Modify Date.: 2023-04-30 11:21
Introduction: antibacterial, anthelmintic; LD50 ip (rat) 63mg/Kg View more+
1. Names and Identifiers
1.1 Name
Hygromycin B
1.2 Synonyms

(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'-[(1S)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)octahydro-4H-spiro[1,3-dioxolo[4,5-c]pyran-2, 2'-pyran]-3',4',5',7-tetrol (non-preferred name) (3'S,4S,4'R,5'S,6R,6'S,7S,7aS)-4-{[(1R,2S,3R,5S,6R)-3-Amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)octahydro-4H-spiro[1,3-dioxolo[4,5-c]pyran-2,2'-py ran]-3',4',5',7-tetrol (non-preferred name) 5-O-(2,3-O-(6-Amino-6-desoxyheptapyranosyliden)-beta-D-talopyranosyl)-desoxy-N'-methyl-D-streptamin antihelmycin D-Streptamine, O-6-amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1→2-3)-O-β-D-talopyranosyl-(1→5)-2-deoxy-N3-methyl- hydromycinb Hygromix Hygromix 2.4 hygromix2.4 hygromix-8 Hygromycin Solution Hygrovetin hygrovetine O-6-Amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1→2-3)-O-β-D-talopyranosyl-(1→5)-2-deoxy-N3-methyl-D-streptamine

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C20H37N3O13 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
897.6 °C at 760 mmHg
2.1 Refractive index
2.1 Flash Point
496.7 °C
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
H2O: 50?mg/mL As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 30 days.
2.2 Appearance
faintly brown to brown powder
2.3 Storage
Keep Cold.
2.4 Chemical Properties
White to off-white lyophilized powder
2.5 Color/Form
faintly brown to brown
2.6 PH
pH (25g/l, 25℃ ) : 9.5~12.5
2.7 pKa
7.1, 8.8(at 25℃)
2.8 Water Solubility
Miscible with water, methanol, buffer solution and ethanol.Immiscible with less polar solvents.
2.9 Stability
Stable at normal temperatures and pressures.
2.10 StorageTemp
3. Use and Manufacturing
3.1 General Description
Amorphous solid or tan powder.
3.2 Methods of Manufacturing
Produced by fermentation of Streptomyces hygroscopicus.
3.3 Usage
antibacterial, anthelmintic; LD50 ip (rat) 63mg/Kg
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Packing Group
4.1 Fire Hazard
Flash point data for Hygromycin B are not available; however Hygromycin B is probably combustible.
4.2 Hazard Class
4.2 Hazard Declaration
H301 + H311-H318-H330-H334
UN 3462
4.2 Safety Profile
Poison byintraperitoneal route. Mutation datareported. When heated to decomposition itemits toxic fumes of Nox Hygromycin BSupplier
4.3 Caution Statement
P260-P280-P284-P301 + P310-P305 + P351 + P338-P310
4.3 WGK Germany
4.3 Specification

The Hygromycin B , with cas registry number of 31282-04-9, also has other registry numbers which are 1403-76-5, 8052-92-4, 8052-93-5. It is also called for Hygrovectine ; Hygromix-8 ; Antihelmycin ; Hygrovetine , and O-6-Amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1-2-3)-o-beta-D-talopyranosyl-(1-5)-2-deoxy-N3-methyl-D-streptamine . Hygromycin B is from streptomyces hygroscopicus. It belongs to the categories of (1) Anthelmintics ; (2) Anti-Bacterial Agents ; (3) Anti-Infective Agents ; (4) Antiparasitic Agents ; (5) Drug / Therapeutic Agent ; (6) Natural Product.

Physical properties of Hygromycin B : (1) ACD/LogP: 0.64 ; (2) # of Rule of 5 Violations: 3 ; (3) ACD/LogD (pH 5.5): -4.36 ; (4) ACD/LogD (pH 7.4): -2.58 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 1 ; (9) #H bond acceptors: 16 ; (10) #H bond donors: 13 ; (11) #Freely Rotating Bonds: 16 ; (12) Index of Refraction: 1.672 ; (13) Molar Refractivity: 118.04 cm3 ; (14) Molar Volume: 315.1 cm3 ; (15) Surface Tension: 103.2 dyne/cm ; (16) Enthalpy of Vaporization: 148.17 kJ/mol.

Uses of Hygromycin B : Hygromycin B , very safe de-worming drug, can effectively kill the roundworm of pigs, whipworm and chickens' roundworm, and have antibacterial effect. And it also can be used for chicken feed (the dosage of 8 (800 × 104U)-12 (1200 × 104U) g / t, Laying disabled, withdrawal period 3 days) and the following 4-month-old pig feed (the dosage of 10 -- 13g / t, withdrawal period of 15 days, to avoid eye contact with human skin).

When you are using this chemical, please be cautious about it as the following:
The Hygromycin B is very toxic by inhalation, in contact with skin and if swallowed. It may cause sensitization by inhalation and skin contact. It has risk of serious damage to the eyes and limited evidence of a carcinogenic effect. Before use it, wear suitable protective clothing, gloves and eye/face protection. Do not breathe vapour and dust. If contact with eyes, rinse immediately with plenty of water and seek medical advice. In case of feel unwell, seek medical advice immediately. It is a poison by intraperitoneal route. When heated to decomposition, it emits toxic fumes of NOx.

You can still convert the following datas into molecular structure:

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 13mg/kg (13mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(5), Pg. 11, 1973.
mouse LD50 intravenous 6mg/kg (6mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 202, 1980.
mouse LD50 oral 46000units/kg (46000units/kg)   Pharmaceutical Chemistry Journal Vol. 1, Pg. 396, 1967.
mouse LDLo intraperitoneal 6mg/kg (6mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacology and Experimental Therapeutics. Vol. 281, Pg. 992, 1997.
rat LC50 inhalation 2220ug/m3/4H (2.22mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION


Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(5), Pg. 11, 1973.
rat LD50 intraperitoneal 63mg/kg (63mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(5), Pg. 11, 1973.

4.4 Toxicity
Celiac-rat LD50: 63 mg/kg; Celiac-guinea pig LD50: 13 mg/kg

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 2

Acute toxicity - Dermal, Category 2

Serious eye damage, Category 1

Acute toxicity - Inhalation, Category 2

Respiratory sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H300 Fatal if swallowed

H310 Fatal in contact with skin

H318 Causes serious eye damage

H330 Fatal if inhaled

H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P262 Do not get in eyes, on skin, or on clothing.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P284 [In case of inadequate ventilation] wear respiratory protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.


P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P310 Immediately call a POISON CENTER/doctor/\u2026

P361+P364 Take off immediately all contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P320 Specific treatment is urgent (see ... on this label).

P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/...


P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


6. Other Information
6.0 Storage Conditions
Produced by fermentation of Streptomyces hygroscopicus.
6.1 Reactive Group
Alcohols and Polyols
6.2 Reactivity Profile
Weakly basic.
6.3 Storage features
Treasury is ventilated, low temperature and dry; stored separately from food materials
6.4 Fire Hazards
Flash point data for this chemical are not available; however it is probably combustible. (NTP, 1992)
6.5 Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
6.6 Personal Protective Equipment
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)
6.7 Mesh
Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)
6.8 First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
6.9 Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
6.10 Usage
An aminoglycoside antibiotic that kills bacteria by inhibiting protein synthesisHygromycin B is used for the selection and maintenance of prokaryotic and eukaryotic cells that contains the hygromycin resistance gene. This gene is frequently used as a selectable marker in research on plants. It stabilizes the transfer ribonucleic acid (tRNA)-ribosomal acceptor site, thereby inhibiting translocation. In addition to this, it serves as an aminoglycosidic antibiotic which inhibits protein synthesis.
6.11 Usage
Hygromycin B was used for hygro resistance effect in the following cells transfected 293T cells with mixture of plasmids at 160 ?g/ml, MCF-7ALOX12 cells at 150 ?g/ml, MSCV Luciferase PGK-hygro plasmid and STAT3 Reporter HeLa Stable Cell Line (stably transfected with Luciferase gene under the control of STAT3 promoter) maintained in DMEM supplemented with 10% FBS. It is suitable for the selection of cells transfected with Escherichia coli hygromycin resistance gene (hyg or hph), as well as for the maintenance of the Hygromycin phenotype of resistant cells. Consistent with its more specific effect on translocation, hygromycin B exhibits monophasic inhibition of polypeptide synthesis, suggesting that it binds to a single site on the ribosome.
7. Computational chemical data
  • Molecular Weight: 527.524g/mol
  • Molecular Formula: C20H37N3O13
  • Compound Is Canonicalized: True
  • XLogP3-AA: -6.6
  • Exact Mass: 527.23263824
  • Monoisotopic Mass: 527.23263824
  • Complexity: 756
  • Rotatable Bond Count: 6
  • Hydrogen Bond Donor Count: 11
  • Hydrogen Bond Acceptor Count: 16
  • Topological Polar Surface Area: 272
  • Heavy Atom Count: 36
  • Defined Atom Stereocenter Count: 16
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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