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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:54:10 UTC
Update Date2019-07-23 06:15:12 UTC
HMDB IDHMDB0034108
Secondary Accession Numbers
  • HMDB34108
Metabolite Identification
Common NameTylosin
DescriptionTylosin, also known as corvel-tylocine or dehydrorelomycin, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. It is found naturally as a fermentation product of Streptomyces fradiae. Tylosin is a very strong basic compound (based on its pKa). Outside of the human body, Tylosin is found, on average, in the highest concentration within milk (cow). This could make tylosin a potential biomarker for the consumption of these foods. Tylosin is a macrolide-class antibiotic used in veterinary medicine. Tylosin is used in treatment of cattle, swine and mycoplasmas in poultry Tylosin is a macrolide-class antibiotic used in veterinary medicine.
Structure
Data?1563862512
Synonyms
ValueSource
Corvel-tylocineHMDB
DehydrorelomycinHMDB
Elanco-mHMDB
FrazidineHMDB
Norco T-2HMDB
ParkenovaHMDB
TylanHMDB
TylonHMDB
Hydrochloride, tylosinMeSH
TylosinMeSH
FradizineMeSH
Tylosin hydrochlorideMeSH
Tylosin tartrate (salt)MeSH
TylosineMeSH
Tartrate, tylosinMeSH
Tylosin tartrateMeSH
Chemical FormulaC46H77NO17
Average Molecular Weight916.1001
Monoisotopic Molecular Weight915.519150043
IUPAC Name2-[(11E,13E)-6-({5-[(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy]-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl}oxy)-16-ethyl-4-hydroxy-15-{[(5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl)oxy]methyl}-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
Traditional Name2-[(11E,13E)-6-({5-[(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy]-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl}oxy)-16-ethyl-4-hydroxy-15-{[(5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl)oxy]methyl}-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
CAS Registry Number1401-69-0
SMILES
CCC1OC(=O)CC(O)C(C)C(OC2OC(C)C(OC3CC(C)(O)C(O)C(C)O3)C(C2O)N(C)C)C(CC=O)CC(C)C(=O)\C=C\C(\C)=C\C1COC1OC(C)C(O)C(OC)C1OC
InChI Identifier
InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+
InChI KeyWBPYTXDJUQJLPQ-LLMNDNAOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Alpha-hydrogen aldehyde
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Cyclic ketone
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Dialkyl ether
  • Oxacycle
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aldehyde
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point131 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.005 mg/mL at 25 °CNot Available
LogP1.63Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP1.46ALOGPS
logP2.32ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area238.67 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity232.21 m³·mol⁻¹ChemAxon
Polarizability98.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0100190762-470bea8fef78f920d2b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008a-1200490300-d317b82ba97107fcfb36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059t-1800590010-9c2e267d4192bf0461adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0981080686-b55a1155803a66b21a13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1500192030-26b62428a4b5cb899691Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-5300090100-13d7422257d01f00b74eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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
FooDB IDFDB012374
KNApSAcK IDNot Available
Chemspider ID4865403
KEGG Compound IDC01457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTylosin
METLIN IDNot Available
PubChem Compound6260974
PDB IDNot Available
ChEBI ID17658
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van der Wolf PJ, Wolbers WB, Elbers AR, van der Heijden HM, Koppen JM, Hunneman WA, van Schie FW, Tielen MJ: Herd level husbandry factors associated with the serological Salmonella prevalence in finishing pig herds in The Netherlands. Vet Microbiol. 2001 Feb 12;78(3):205-19. [PubMed:11165065 ]
  2. Harvey RB, Edrington TS, Kubena LF, Corrier DE, Elissalde MH: Influence of the antibiotics lincomycin and tylosin on aflatoxicosis when added to aflatoxin-contaminated diets of growing swine. J Vet Diagn Invest. 1995 Jul;7(3):374-9. [PubMed:7578454 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .