Tiamulin (CHEM019189)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:53:48 UTC
Update Date2016-11-09 01:15:56 UTC
Accession NumberCHEM019189
Identification
Common NameTiamulin
ClassSmall Molecule
DescriptionA carbotricyclic compound that is pleuromutilin in which the hydroxyacetate group is replaced by a 2-{[2-(diethylamino)ethyl]sulfanyl}acetate group. An antibacterial drug, tiamulin is used in veterinary medicine (generally as its hydrogen fumarate salt) for the treatment of swine dysentery caused by Serpulina hyodysenteriae.
Contaminant Sources
  • STOFF IDENT Compounds
  • Suspected Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TiamulinaChEBI
TiamulineChEBI
TiamulinumChEBI
DenagardKegg
Tiamulin fumarate (1:1), (3as-(3aalpha,4beta,5alpha,6alpha,8beta,9alpha,9abeta,10S*))-isomerMeSH
Tiamulin hydrochlorideMeSH
2-(Diethylaminoethyl)thioacetoxymutilinMeSH
TiamutinMeSH
DynamutilinMeSH
Tiamulin fumarateMeSH
Chemical FormulaC28H47NO4S
Average Molecular Mass493.742 g/mol
Monoisotopic Mass493.323 g/mol
CAS Registry Number55297-95-5
IUPAC Name(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate
Traditional Nametiamulin
SMILES[H][C@@]12C(=O)CC[C@]11CC[C@@]([H])(C)[C@@]2(C)[C@@]([H])(C[C@@](C)(C=C)[C@@]([H])(O)[C@]1([H])C)OC(=O)CSCCN(CC)CC
InChI IdentifierInChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1
InChI KeyUURAUHCOJAIIRQ-QGLSALSOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentPleuromutilin and derivatives
Alternative Parents
Substituents
  • Pleuromutilin
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkylthioether
  • Sulfenyl compound
  • Monocarboxylic acid or derivatives
  • Thioether
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00052 g/LALOGPS
logP4.47ALOGPS
logP4.5ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.43ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.84 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity140.74 m³·mol⁻¹ChemAxon
Polarizability56.81 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-1910000000-dcba10789dcdb073f414Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900300000-69e826135bba34d65b0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-330cc01e25deade8bdcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0910000000-7a7403b84fe0b950a42eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-0900000000-680b97999b88640ad153Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0000900000-93e5960b0d906f842e50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fc3-1902600000-409e6680254750fff1ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-3927500000-1c498cb1b0798694c8bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9610000000-777b67131361fa1376c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-1409600000-e9db1bb9dace00b99e90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fry-5609200000-84e8eb0cdce3f05fb1f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-9213000000-1e211c7b35c5492d1c23Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11468
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTiamulin
Chemspider IDNot Available
ChEBI ID44137
PubChem Compound ID656958
Kegg Compound IDC12065
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15013817
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16253666
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25592328
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3170319
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3686511