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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:01:57 UTC
Update Date2019-01-11 19:48:07 UTC
HMDB IDHMDB0034229
Secondary Accession Numbers
  • HMDB34229
Metabolite Identification
Common NameHygromycin B
DescriptionHygromycin 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
Data?1547236086
Synonyms
ValueSource
Antibiotic a-396-IIHMDB
AntihelmycinHMDB
HyanthelmixHMDB
Hydromycin bHMDB
Hygromix 2.4HMDB
Hygromix-8HMDB
HygrovectineHMDB
HygrovetineHMDB
b, HygromycinMeSH
Chemical FormulaC20H37N3O13
Average Molecular Weight527.5201
Monoisotopic Molecular Weight527.232638285
IUPAC Name4-{[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 Name4-{[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 Number31282-04-9
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 KeyGRRNUXAQVGOGFE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent2-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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point160 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility213 g/LALOGPS
logP-2.9ALOGPS
logP-6.5ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)11.41ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area272.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity114.05 m³·mol⁻¹ChemAxon
Polarizability51.86 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-022j-9214410000-b96596b899ba5b2cc3d5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03du-9430407000-b093ee569d51038e7e88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0900260000-1761665bcbd467944228View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2900100000-8b57f5e32f01f8d04e06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-9700000000-779e590d50eaeaf6212fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fai-1900010000-e8f4085343959574ed17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1902210000-6429be7cdc080fcd0e5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5900000000-627ee8af8669f6234340View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012540
KNApSAcK IDNot Available
Chemspider ID3532
KEGG Compound IDC01925
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHygromycin B
METLIN IDNot Available
PubChem Compound3659
PDB IDNot Available
ChEBI ID16976
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .