ChemFOnt: Showing chemical card for Hygromycin B (CFc000015307)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:25 UTC

Chemfont ID

CFc000015307

Molecule Identification

Common Name

Hygromycin B

Definition

Hygromycin B is a fda approved antibiotic food additive for swine and poultry Hygromycin B is an antibiotic produced by the bacterium Streptomyces hygroscopicus. It is an aminoglycoside that kills bacteria, fungi and higher eukaryotic cells by inhibiting protein synthesis. In the laboratory it is used for the selection and maintenance of prokaryotic and eukaryotic cells that contain the hygromycin resistance gene. The resistance gene is a kinase that inactivates hygromycin B through phosphorylation. Since the discovery of hygromycin-resistance genes, hygromycin B has become a standard selection antibiotic in gene transfer experiments in many prokaryotic and eukaryotic cells

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Antibiotic a-396-II	HMDB
Antihelmycin	HMDB
Hyanthelmix	HMDB
Hydromycin b	HMDB
Hygromix 2.4	HMDB
Hygromix-8	HMDB
Hygrovectine	HMDB
Hygrovetine	HMDB
b, Hygromycin	MeSH, HMDB
Hygromycin b	MeSH

Chemical Formula

C₂₀H₃₇N₃O₁₃

Average Molecular Weight

527.5201

Monoisotopic Molecular Weight

527.232638285

IUPAC Name

4-{[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)-tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol

Traditional Name

4-{[3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy}-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)-tetrahydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol

CAS Registry Number

31282-04-9

SMILES

CNC1CC(N)C(O)C(OC2OC(CO)C(O)C3OC4(OC23)OC(C(N)CO)C(O)C(O)C4O)C1O

InChI Identifier

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

InChI Key

GRRNUXAQVGOGFE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-deoxystreptamine aminoglycosides. These are aminoglycosides containing the 2-deoxystreptamine (1,3-diaminocyclohexane-4,5,6-triol) core.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

2-deoxystreptamine aminoglycosides

Alternative Parents

Substituents

2-deoxystreptamine aminoglycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Dioxolopyran
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Carboxylic acid orthoester
Ortho ester
Cyclitol or derivatives
Oxane
Cyclic alcohol
Meta-dioxolane
Orthocarboxylic acid derivative
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Organoheterocyclic compound
Oxacycle
Acetal
Secondary aliphatic amine
Polyol
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Primary alcohol
Primary amine
Amine
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

amino cyclitol (CHEBI:4454 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034229)
Cytoplasm (HMDB: HMDB0034229)

Source

Exogenous

Exogenous (HMDB: HMDB0034229)

Food

Food (HMDB: HMDB0034229)

Process

Not Available

Role

Industrial application

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0034229)

Biological role

Nutrient (HMDB: HMDB0034229)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	213 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-6.5	ChemAxon
logS	-0.39	ALOGPS
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	272.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.05 m³·mol⁻¹	ChemAxon
Polarizability	51.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon