Hygrovetine

HCID 35766

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Basic information

CAS: 31282-04-9
Standard SMILES: CN[C@H]1C[C@@H](N)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@@H]3OC4(O[C@H]23)O[C@H]([C@@H](N)CO)[C@H](O)[C@@H](O)[C@H]4O)[C@@H]1O
InChIKey: GRRNUXAQVGOGFE-KPBUCVLVSA-N
Molecular formula: C20H37N3O13
Average molar mass: 527.5 g/mol

Overview

Hygromycin-B has been reported in Nocardia abscessus with data available.

Names & identifiers

Preferred name: Hygrovetine
IUPAC: (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
English name: Hygromycin B
Molecular formula: C20H37N3O13
Molecular weight: 527.52

Names & synonyms

HygrovetineHygrovectineMFCD06795479HYGROMYCIN-Borb93633SCHEMBL3109orb1734998GRRNUXAQVGOGFE-KPBUCVLVSA-NGLXC-25648AKOS026750002NS00011531Q418735

Show more names

HYGROMYCIN B HYDRATE950U/MGHygromixHygrovetinhygromix-8hygromix2.4hydromycinbantihelmycinHygromycin B

(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)cyclohexoxy]-6'-[(1S)-1-amino-2-hydroxy-ethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-tetrahydropyran]-3',4',5',7-tetrolO-6-Amino-6-deoxy-L-glycero-D-galacto-heptopyranosylidene-(1->2- 3)-O-.alpha.-D-talopyranosyl-(1->5)-2-deoxy-N3-

Database identifiers

CAS: 31282-04-9
PubChem CID: 35766

Properties

Computed structural properties

XLogP: -6.6
Topological polar surface area: 272 Å²
Hydrogen bond donors: 11
Hydrogen bond acceptors: 16
Rotatable bonds: 6
Heavy atoms: 36
Formal charge: 0
Complexity: 756

Experimental & physicochemical properties

DrugsPharmaceuticals -> Antibiotics

Physicochemical properties

Melting point: 160 · 160-180°C
alpha: 20 · D20 +20.2° (c = 1 in water)
Boiling point: 608.13 °C · 608.13°C (rough estimate)
Density: 1.4252 · 1.4252 (rough estimate)
refractive index: 1.63 · 1.6300 (estimate)
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: 50 mg/mL As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 30 days.
form: powder
pka: 7.1 · 7.1, 8.8(at 25℃)
color: faintly brown to brown
PH: pH (25g/l, 25℃ ) : 9.5～12.5
biological source: Streptomyces hygroscopicus
Water Solubility: Miscible with water, methanol, buffer solution and ethanol. Immiscible with less polar solvents.
Merck: 14 · 14,4852
BRN: 6755837 · 6755837
Stability: Hygroscopic
InChIKey: GRRNUXAQVGOGFE-KPBUCVLVSA-N
FDA 21 CFR: 556.33 · 556.330; 558.274; 558.4
FDA UNII: 3 XQ2233B0B · 3XQ2233B0B
EPA Substance Registry System: Hygromycin B (31282-04-9)
UNSPSC Code: 51281624 · 51281624
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 300 · H300+H330
Precautionary statements: 260 · P260-P264-P270-P271-P284-P304+P340+P310
Hazard Codes: T+,Xn,T
Risk Statements: 26 · 26/27/28-41-42/43-40-36-23/24/25
Safety Statements: 23 · 23-26-28-36/37/39-45-22-36-36/37
RIDADR: 3462 · UN 3462 6.1/PG 1
WGK Germany: 3 · 3
RTECS: 2130000 · WK2130000
F: 19 · 19
HazardClass: 6.1 · 6.1
PackingGroup: I
HS Code: 29419059 · 29419059
Storage Class: 6.1 B · 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 1 InhalationAcute · Acute Tox. 1 InhalationAcute Tox. 3 OralAcute Tox. 4 Dermal
Toxicity: 250 mg/L · mmo-esc 250 mg/L AACHAX 18,798,80

Safety & regulation

Safety data

F: 19
wgk: 3
rtecs: WK2130000
ridadr: UN 3462 6.1/PG 1
hs_code: 29419059
Toxicity: mmo-esc 250 mg/L AACHAX 18,798,80
risk_code: 26/27/28-41-42/43-40-36-23/24/25
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+,Xn,T
safety_code: 23-26-28-36/37/39-45-22-36-36/37
hazard_class: 6.1
Storage Class: 6.1B - Non-combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: I
Hazard statements: H300+H330
Hazard Classifications: Acute Tox. 1 InhalationAcute Tox. 3 OralAcute Tox. 4 Dermal
Precautionary statements: P260-P264-P270-P271-P284-P304+P340+P310

Chemistry & industry

Applications · 6 items

DescriptionHygromycin B is an aminoglycoside antibiotic that has been found in S. hygroscopicus. It is active against E. coli (MIC = 150 μg/ml) and cytotoxic to both prokaryotic and eukaryotic cells via inhibition of protein synthesis. Hygromycin B has commonly been used in molecular and cell biology applications to select for transformed cells expressing the E. coli hygromycin resistance genes hyg or hph.

Usesantibacterial, anthelmintic; LD50 ip (rat) 63mg/Kg

UsesHygromycin B, a selective antibiotic that is effective on most bacteria, fungi and higher eukaryotes, inhibits protein synthesis by interfering with translocation and causing mistranslation at the 70S ribosome

UsesHygromycin B is an aminoglycoside and a selective antibiotic agent for the hph gene. Hygromycin B inhibits protein synthesis by interfering with translocation and causing mistranslation at the 70S rib osome

UsesHygromycin B is a trisaccharide aminoglycoside with a terminal cyclitol produced by Streptomyces hygroscopicus, reported by researchers at Eli Lily in the early 1950s. Hygromycin B belongs to the destomycin family of aminoglycosides which contain a unique cyclic structure linking the terminal saccharide. Hygromycin B exhibits broad spectrum antibiotic and anthelmintic activity, and is used as a feed additive for swine and poultry. Hygromycin B inhibits polypeptide synthesis by binding peptidyl-tRNA and preventing translocation by Elongation Factor 2.

General DescriptionAmorphous solid or tan powder.